2021/08/06 更新

写真a

ホシ タカシ
星 隆
HOSHI Takashi
所属
教育研究院 自然科学系 生産デザイン工学系列 准教授
工学部 工学科 准教授
職名
准教授
外部リンク

学位

  • 博士(理学) ( 1996年3月   東北大学 )

研究分野

  • ナノテク・材料 / 有機合成化学

経歴(researchmap)

  • 新潟大学   自然科学研究科 材料生産システム専攻   助教

    2004年4月 - 現在

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  • 新潟大学   自然科学研究科 材料生産システム専攻   助教

    2004年4月 - 現在

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  • 新潟大学   工学部 化学システム工学科   助教

    2004年4月 - 現在

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  • 新潟大学   自然科学研究科   助手

    1998年4月 - 2000年3月

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  • 新潟大学 工学部 化学システム工学プログラム   助教

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経歴

  • 新潟大学   工学部 工学科   准教授

    2020年2月 - 現在

  • 新潟大学   工学部 工学科   助教

    2017年4月 - 2020年1月

  • 新潟大学   自然科学研究科 材料生産システム専攻   助教

    2004年4月 - 2020年1月

  • 新潟大学   自然科学研究科 材料生産システム専攻   助教

    2004年4月 - 2020年1月

  • 新潟大学   化学システム工学科   助教

    2004年4月 - 2017年3月

  • 新潟大学   自然科学研究科   助手

    1998年4月 - 2000年3月

▶ 全件表示

 

論文

  • Suzukimiyaura coupling reactions using low loading of ligand-activated palladium catalyst by cooperative copper catalysis

    Takashi Hoshi, Yuka Shishido, Ayumi Suzuki, Yuki Sasaki, Hisahiro Hagiwara, Toshio Suzuki

    Chemistry Letters   47 ( 6 )   780 - 783   2018年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Chemical Society of Japan  

    A highly active Pd/Cu cooperative catalytic system based on biphenylene-substituted di-tert-butylruthenocenylphosphine (R-Phos) was developed for performing SuzukiMiyaura coupling reactions of (hetero)aryl, alkenyl, and benzyl bromides with (hetero)arylboronic acid pinacol esters. A variety of sterically and/or electronically diverse bromides and boronate esters were successfully coupled in good to excellent yields at room temperature using 0.1 mol % Pd and 5 mol % Cu.

    DOI: 10.1246/cl.180185

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  • A diastereomeric pair of sulfoxide-containing chiral MOP-type ligands: Preparation and application to rhodium-catalyzed asymmetric 1,4-addition reactions

    Takashi Hoshi, Masataka Fujita, Shouta Matsushima, Hisahiro Hagiwara, Toshio Suzuki

    Chemistry Letters   47 ( 6 )   800 - 802   2018年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Chemical Society of Japan  

    (R,SS)-Sulfoxide-MOP (L2) and (R,RS)-sulfoxide-MOP (L3) were developed as a diastereomeric pair of sulfoxide-containing chiral MOP-type ligands. These two ligands also represent the first monosulfoxide analogues of BINAP. The chiral ligand L2 was successfully applied to the highly enantioselective rhodium-catalyzed 1,4-addition between α,β-unsaturated ketones or esters and arylboronic acids, and exhibited a broad substrate scope when the reaction was performed using 1.5 mol% Rh in cyclohexane/H2O (10:1) at 40 °C under mild basic conditions.

    DOI: 10.1246/cl.180260

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  • An Active, General, and Long-Lived Palladium Catalyst for Cross-Couplings of Deactivated (Hetero)aryl Chlorides and Bromides with Arylboronic Acids

    Takashi Hoshi, Tomonobu Honma, Ayako Mori, Maki Konishi, Tsutomu Sato, Hisahiro Hagiwara, Toshio Suzuki

    JOURNAL OF ORGANIC CHEMISTRY   78 ( 22 )   11513 - 11524   2013年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    An active, general, and long-lived palladium catalyst for Suzuki-Miyaura reactions of aryl and heteroaryl chlorides deactivated by steric hindrance, electron richness, and coordinating functional groups is reported. In reactions of arylbromide bearing two o-tert-butyl substituents, C(sp(3))-H arylation of the tert-butyl group, rather than the Suzuki-Miyaura reaction, proceeded in excellent yield. The key to the success of the reactions was the development of biphenylene-substituted dicyclohexylruthenocenylphosphine (CyR-Phos) as a supporting ligand.

    DOI: 10.1021/jo402089r

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  • Second generation synthesis of the neo-clerodane diterpenoid methyl barbascoate

    Hisahiro Hagiwara, Naomi Honma, Kimihiko Kinugawa, Shota Sato, Takashi Hoshi, Toshio Suzuki

    Natural Product Communications   8 ( 7 )   873 - 875   2013年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    The second generation total synthesis of the neo-clerodane diterpenoid, methyl barbascoate, was accomplished in seven or nine linear steps via double enol triflation and subsequent palladium catalyzed double carbonylation, followed by regioselective samarium diiodide mediated conjugate reduction.

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  • Expedient synthesis of (E)-3-methylcyclopentadec-2-en-1-one, an important precursor for (R)-(-)muscones

    Hisahiro Hagiwara, Teppei Adachi, Masaharu Doya, Takashi Hoshi, Toshio Suzuki

    FLAVOUR AND FRAGRANCE JOURNAL   27 ( 1 )   54 - 59   2012年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY-BLACKWELL  

    An expedient synthesis of (E)-3-methylcyclopentadec-2-en-1-one, an important precursor for (R)-(-)-muscone, was developed. The key steps were vapour-phase intramolecular aldol condensation catalysed by zinc oxide at 360 degrees C followed by double bond isomerization by the additionelimination of hydrogen chloride. Copyright (C) 2011 John Wiley & Sons, Ltd.

    DOI: 10.1002/ffj.2080

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  • Erratum: A highly sustainable and active catalyst for Suzuki-Miyaura reaction: Palladium-supported ionic liquid catalyst (SILC) coated with polymer (Synlett (2011) (2545))

    Hisahiro Hagiwara, Kota Sato, Takashi Hoshi, Toshio Suzuki

    Synlett   2905   2011年11月

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  • A Highly Sustainable and Active Catalyst for Suzuki-Miyaura Reaction: Palladium-Supported Ionic Liquid Catalyst (SILC) Coated with Polymer

    Hisahiro Hagiwara, Kota Sato, Takashi Hoshi, Toshio Suzuki

    SYNLETT   ( 17 )   2545 - 2550   2011年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:GEORG THIEME VERLAG KG  

    With the aid of an ionic liquid, palladium acetate was immobilized in the pores of silica gel, which was coated with polyethylene terephthalate. The heterogeneous catalyst was effective for Suzuki-Miyaura reactions of ortho-substituted aryl bromides, aryl triflates, and arylboronic acids in aqueous ethanol at room temperature, and could be re-used up to ten times.

    DOI: 10.1055/s-0030-1260322

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  • First total syntheses of bicyclic marine sesquiterpenoids drechslerines A and B

    Hisahiro Hagiwara, Masakazu Fukushima, Kimihiko Kinugawa, Takuya Matsui, Takashi Hoshi, Toshio Suzuki

    TETRAHEDRON   67 ( 22 )   4061 - 4068   2011年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    The first total syntheses of the bicyclic sesquiterpenoids drechslerines A (1) and B (2), which were isolated from the algicolous fungus Drechslera dematioidea in the marine red alga Liagora viscida, has been accomplished starting from (S)-carvone (13) via three palladium-catalyzed reactions, namely, diastereoselective allylation, conjugate reduction, and carbon monoxide insertion, as the key reactions. (C) 2011 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2011.04.007

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  • Highly Enantioselective Pd-Catalyzed Allylic Alkylation of Indoles Using Sulfur-MOP Ligand

    Takashi Hoshi, Koji Sasaki, Shun Sato, Yuichi Ishii, Toshio Suzuki, Hisahiro Hagiwara

    ORGANIC LETTERS   13 ( 5 )   932 - 935   2011年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    The preparation of various (R)-Sulfur-MOP ligands with aryl and alkyl substituents on sulfur, and the application of these ligands to Pd-catalyzed asymmetric allylic alkylation of indoles is reported. The sulfur substituent served as an effective stereocontrol element, and in the case of the 2-i-PrPh substituent on sulfur, the allylation products from an array of simple and substituted indoles were obtained with high enantioselectivity (up to 95% ee).

    DOI: 10.1021/ol102977b

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  • Palladium-supported ionic liquid catalyst (Pd-SH-SILC) immobilized on mercaptopropyl silica gel as a chemoselective, reusable and heterogeneous catalyst for catalytic hydrogenation

    Hisahiro Hagiwara, Tomomi Nakamura, Takashi Hoshi, Toshio Suzuki

    GREEN CHEMISTRY   13 ( 5 )   1133 - 1137   2011年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    Palladium acetate was immobilized as Pd-SH-SILC (Pd-supported ionic liquid catalyst) in the pores of amorphous mercaptopropyl silica gel with the aid of an ionic liquid [bmim] BF(4). The heterogeneous Pd-SH-SILC was effective for catalytic hydrogenation of a variety of olefins at atmospheric pressure and room temperature. It withstood recycling up to 10 times by decantation.

    DOI: 10.1039/c1gc15217c

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  • First total synthesis of the neo-clerodane diterpenoid salvinorin F

    Hisahiro Hagiwara, Takashi Nojima, Yuhki Suka, Takashi Hoshi, Toshio Suzuki

    Natural Product Communications   6 ( 3 )   333 - 335   2011年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    The total synthesis of the neo-clerodane diterpenoid salvinorin F was accomplished for the first time.

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  • Total synthesis of the bicyclic marine sesquiterpenoid drechslerine B

    Hisahiro Hagiwara, Masakazu Fukushima, Kimihiko Kinugawa, Takuya Matsui, Takashi Hoshi, Toshio Suzuki

    Natural Product Communications   6 ( 3 )   311 - 313   2011年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    The total synthesis of the recently isolated bicyclic sesquiterpenoid drechslerine B (2), isolated from the algicolous fungus Drechslera dematioidearare in the marine red alga Liagora viscida, has been achieved, starting from (8)-carvone (8), via an intramolecular aldol reaction and palladium-catalyzed carbon monoxide insertion as key reactions.

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  • Immobilization of Pd on Nanosilica Dendrimer as SILC: Highly Active and Sustainable Cluster Catalyst for Suzuki-Miyaura Reaction

    Hisahiro Hagiwara, Hirokazu Sasaki, Norio Tsubokawa, Takashi Hoshi, Toshio Suzuki, Tetsuya Tsuda, Susumu Kuwabata

    SYNLETT   ( 13 )   1990 - 1996   2010年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:GEORG THIEME VERLAG KG  

    Palladium acetate was noncovalently immobilized as a supported ionic liquid catalyst (SILC) in a nanosilica dendrimer, PAMDMAM, with the aid of an ionic liquid to form a cluster catalyst of palladium nanoparticles. The pseudo-homogeneous heterogenized catalyst, Pd-nanoPAMDMAM-SILC, was effective for Suzuki-Miyaura reactions of ortho-substituted aryl bromides or aryl triflates without a ligand in 50% aqueous ethanol in air at room temperature. The catalyst could be re-used up to five times in 93% average yield after simple centrifugation. TON reached 176,000.

    DOI: 10.1055/s-0029-1219816

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  • Immobilization of MacMillan Imidazolidinone as Mac-SILC and its Catalytic Performance on Sustainable Enantioselective Diels-Alder Cycloaddition

    Hisahiro Hagiwara, Toshihiro Kuroda, Takashi Hoshi, Toshio Suzuki

    ADVANCED SYNTHESIS & CATALYSIS   352 ( 5 )   909 - 916   2010年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY-V C H VERLAG GMBH  

    MacMillan's imidazolidinone catalyst was immobilized as a supported ionic liquid catalyst (Mac-SILC) in the pores of silica gel with the aid of an ionic liquid 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide. The heterogenized organocatalyst was utilized for the enantioselective Diels-Alder reaction of cyclopentadiene and cinnamaldehyde, recovered by simple filtration and subsequent evacuation, and repeatedly used up to six times in 81% average chemical yield, 87% ee for endo- and 80% ee for exo-products. The Mac-SILC was effective for a variety of substrates.

    DOI: 10.1002/adsc.200900865

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  • Catalytic Performance of Ruthenium-Supported Ionic-Liquid Catalysts in Sustainable Synthesis of Macrocyclic Lactones

    Hisahiro Hagiwara, Tomomi Nakamura, Naotaro Okunaka, Takashi Hoshi, Toshio Suzuki

    HELVETICA CHIMICA ACTA   93 ( 1 )   175 - 182   2010年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY-V C H VERLAG GMBH  

    Thirteen- to eighteen-membered lactones were synthesized by ring-closing olefin-metathesis reactions of bis-olefins with heterogeneous Grubbs-supported ionic-liquid catalysts (SILCs), in which homogeneous Grubbs catalysts were confined in pores of alumina with the aid of an ionic liquid. The Grubbs-SILCs exhibited higher catalytic performance than their homogeneous counterparts and could be repeatedly recovered by simple filtration and re-used several times.

    DOI: 10.1002/hlca.200900334

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  • Erratum: Sustainable click reaction catalyzed by Supported Ionic Liquid Catalyst (Cu-SILC) (Synlett (2009) (643))

    Hisahiro Hagiwara, Hirokazu Sasaki, Takashi Hoshi, Toshio Suzuki

    Synlett   3224   2009年12月

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  • Nano-silica PAMAM Dendrimer as a Novel Catalyst for Knoevenagel Reactions

    Hisahiro Hagiwara, Masayoshi Sekifuji, Norio Tsubokawa, Takashi Hoshi, Toshio Suzuki

    CHEMISTRY LETTERS   38 ( 9 )   926 - 927   2009年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    A nano-silica dendrimer, poly(amidoamine)-grafted nanosilica (nano-PAMAM), catalyzed the Knoevenagel reaction of aryl and aliphatic aldehydes with various active methylene compounds at room temperature in good yields. The reaction conditions were mild enough that base-sensitive AcO or acid-sensitive THPO groups remained intact in the products. The catalyst was recycled up to 4 times in 78% average yield.

    DOI: 10.1246/cl.2009.926

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  • Henry Reaction Catalyzed by Aminopropylated Nanosilica

    Hisahiro Hagiwara, Masayoshi Sekifuji, Norio Tsubokawa, Takashi Hoshi, Toshio Suzuki

    CHEMISTRY LETTERS   38 ( 8 )   790 - 791   2009年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    The Henry reaction was catalyzed by 0.01 equiv of amino-propylated nanosilica particles (nano-NAP) in refluxing nitro alkanes to provide nitrostyrenes in good yields. The catalyst could be recycled up to three times in 76% average yield.

    DOI: 10.1246/cl.2009.790

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  • Second-generation synthesis of salvinorin A

    Hisahiro Hagiwara, Yuhki Suka, Takashi Nojima, Takashi Hoshi, Toshio Suzuki

    TETRAHEDRON   65 ( 25 )   4820 - 4825   2009年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Functionalization toward total synthesis of the hallucinogenic neoclerodane diterpenoid salvinorin A was accomplished via three double sequences: bis-enol triflate synthesis, palladium-catalyzed double carbonylation to the bis-enol triflate, and samarium diiodide-mediated double conjugate reduction. The configuration at C-12 was controlled by chelation-controlled diastereoselective reduction. (C) 2009 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2009.04.053

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  • Biphenylene-Substituted Ruthenocenylphosphine for Suzuki-Miyaura Coupling of Sterically Hindered Aryl Bromides

    Takashi Hoshi, Ippei Saitoh, Taichi Nakazawa, Toshio Suzuki, Jun-ichi Sakai, Hisahiro Hagiwara

    JOURNAL OF ORGANIC CHEMISTRY   74 ( 10 )   4013 - 4016   2009年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    A highly general, active, and stable catalytic system was realized in the palladium-catalyzed Suzuki-Miyaura reactions of sterically hindered aryl bromides with arylboronic acids using biphenylene-substituted di-tert-butylruthenocenylphosphine (R-Phos) as a supporting ligand.

    DOI: 10.1021/jo900550g

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  • Sustainable Click Reaction Catalyzed by Supported Ionic Liquid Catalyst (Cu-SILC)

    Hisahiro Hagiwara, Hirokazu Sasaki, Takashi Hoshi, Toshio Suzuki

    SYNLETT   ( 4 )   643 - 647   2009年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:GEORG THIEME VERLAG KG  

    Cuprous bromide was immobilized as a copper-supported ionic liquid catalyst (Cu-SILC) in the pores of amorphous mercaptopropyl silica gel with the aid of an ionic liquid, [bmim]PF(6). The heterogeneous Cu-SILC effectively and regioselectively catalyzed Huisgen [3+2] cycloadditions at room temperature in aqueous ethanol, and was used LIP to six times after simple decantation.

    DOI: 10.1055/s-0028-1087926

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  • Immobilization of Grubbs catalyst as supported ionic liquid catalyst (Ru-SILC)

    Hisahiro Hagiwara, Naotaro Okunaka, Takashi Hoshi, Toshio Suzuki

    SYNLETT   ( 12 )   1813 - 1816   2008年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:GEORG THIEME VERLAG KG  

    Grubbs olefin metathesis catalyst was immobilized as a ruthenium-supported ionic liquid catalyst (Ru-SILC) in pores of amorphous alumina with the aid of ionic liquid [hmim]PF(6). This Ru-SILC was effective for various olefin metathesis reactions such as intra- or intermolecular macrocyclization and dimerization, and used up to six times after simple decantation.

    DOI: 10.1055/s-2008-1078570

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  • Expedient mukaiyama-type Mannich reaction catalyzed by lithium chloride

    Hisahiro Hagiwara, Daiki Iijima, Bahlul Z. S. Awen, Takashi Hoshi, Toshio Suzuki

    SYNLETT   ( 10 )   1520 - 1522   2008年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:GEORG THIEME VERLAG KG  

    The Mannich reaction of methylsilyl enol ether with arylaldimine proceeded in the presence of a catalytic amount of lithium chloride in dimethylformamide at room temperature. The reaction was mild enough to apply to aldimines having the AcO, TBDMSO, or MeS group. Microwave irradiation accelerated the reaction substantially to reduce reaction time. microwave heating.

    DOI: 10.1055/s-2008-1078424

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  • Biphenylene-substituted ruthenocenylphosphine for Suzuki-Miyaura coupling of aryl chlorides

    Takashi Hoshi, Taichi Nakazawa, Ippei Saitoh, Ayako Mori, Toshio Suzuki, Jun-ichi Sakai, Hisahiro Hagiwara

    ORGANIC LETTERS   10 ( 10 )   2063 - 2066   2008年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    High activity in the palladium-catalyzed Suzuki-Miyaura reactions of aryl chlorides with arylboronic acids was furnished using biphenylene-substituted di-tert-butylruthenocenylphosphine (R-Phos) as a supporting ligand. Substrate combinations even for the construction of highly hindered tetra- ortho-substituted biaryls can be achieved in good to excellent yields with low catalyst loadings in short reaction times.

    DOI: 10.1021/ol800567q

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  • Expedient synthetic transformation of ptychantins into forskolin

    Hisahiro Hagiwara, Masashi Tsukagoshi, Takashi Hoshi, Toshio Suzuki, Toshihiro Hashimoto, Yoshinori Asakawa

    SYNLETT   ( 6 )   929 - 931   2008年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:GEORG THIEME VERLAG KG  

    Forskolin has been synthesized in 11 steps with a 17% overall yield from ptychantins A and B, which have been isolated from the liverwort Ptychanthus striatus in good yield. The I a-hydroxy group was furnished by stereoselective reduction of the corresponding carbonyl group by sodium cyanoborohydride. The 9 alpha-hydroxy group was introduced stereoselectively by epoxidation of Delta(9,11)-enol ether.

    DOI: 10.1055/s-2008-1042930

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  • Total synthesis of the hallucinogenic neoclerodane diterpenoid salvinorin A

    Masato Nozawa, Yuhki Suka, Takashi Hoshi, Toshio Suzuki, Hisahiro Hagiwara

    ORGANIC LETTERS   10 ( 7 )   1365 - 1368   2008年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Total synthesis of salvinorin A (1), a neoclerodane diterpenoid having the most potent hallucinogenic activity and a selective K-opioid agonist, was completed in 20 steps starting from enantiomerically pure hydroxy-Wieland-Miescher ketone 5.

    DOI: 10.1021/ol800101v

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  • Sustainable Suzuki-Miyaura reaction catalyzed by Pd(OAc)(2) immobilized on reversed-phase alumina

    Hisahiro Hagiwara, Keon Hyeok Ko, Takashi Hoshi, Toshio Suzuki

    SYNLETT   ( 4 )   611 - 613   2008年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:GEORG THIEME VERLAG KG  

    Employing Pd(OAC)(2) immobilized on amorphous N,N-diethylaminopropyl alumina, Suzuki-Miyaura coupling of aryl halide with arylboronic acid was realized in 50% aqueous ethanol at room temperature, which enabled repeated use up to four times in 96% average yield and achieved a turnover number of 15 000.

    DOI: 10.1055/s-2008-1032081

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  • Sustainable conjugate addition of indoles catalyzed by acidic ionic liquid immobilized on silica

    Hisahiro Hagiwara, Masayoshi Sekifuji, Takashi Hoshi, Toshio Suzuki, Bao Quanxi, Kun Qiao, Chiaki Yokoyama

    SYNLETT   ( 4 )   608 - 610   2008年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:GEORG THIEME VERLAG KG  

    A new protocol for 1,4-conjugate addition of indoles to vinyl ketones has been developed, employing Lewis acidic ionic liquid immobilized on silica, ILIS-SO(2)Cl, as a catalyst, which exhibited an efficient, mild and recyclable nature. The reaction condition is applicable to various vinyl ketones and indoles. The mild nature of the reaction condition showed that the acetoxy or TBDMS group in indoles was maintained intact. The catalyst was used six times resulting in 86% average yield.

    DOI: 10.1055/s-2008-1032082

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  • Total synthesis of valeriananoids A, B, and C via autocatalytic diastereoselective domino Michael reaction

    Masakazu Fukushima, Akihiro Morii, Takashi Hoshi, Toshio Suzuki, Hisahiro Hagiwara

    TETRAHEDRON   63 ( 30 )   7154 - 7164   2007年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Natural enantiomers of unique tricyclic sesquiterpenoids, valeriananoids A-C 1-3, have been synthesized starting from bicyclo[2.2.2]octane-2,5-dione derivative 11, which was obtained by diastereoselective catalytic domino Michael reaction of oxophorone 5 with 8-phenylmenthyl acrylate 10 by LDA or silica-gel-base (NMAP-Li). The tricyclic ring was closed selectively by intramolecular 6-endo-trig mode cyclization of the ketyl radical, which was generated from keto-allylether 25 by either lithium or sodium naphthalenide. (C) 2007 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2007.04.095

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  • Synthesis of bis(indolyl)methanes catalyzed by acidic ionic liquid immobilized on silica (ILIS)

    Hisahiro Hagiwara, Masayoshi Sekifuji, Takashi Hoshi, Kun Qiao, Chiaki Yokoyama

    SYNLETT   ( 8 )   1320 - 1322   2007年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:GEORG THIEME VERLAG KG  

    A new organocatalytic procedure for the synthesis of bis(indolyl)methanes with acidic ionic liquid immobilized on silica gel (ILIS-SO2Cl) has been developed. The reaction condition is applicable to a variety of aryl and aliphatic aldehydes and indoles. The mild nature of the reaction conditions showed that the acetoxy or TBDMS group in the aldehyde was maintained intact. The catalyst was reused four times in 93% average yield.

    DOI: 10.1055/s-2007-977453

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  • Recyclable asymmetric cyclization in ionic liquid catalyzed by an amino acid, leading to a Wieland-Miescher ketone analogue

    Masato Nozawa, Tetsuya Akita, Takashi Hoshi, Toshio Suzuki, Hisahiro Hagiwara

    SYNLETT   ( 4 )   661 - 663   2007年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:GEORG THIEME VERLAG KG  

    A procedure for recyclable asymmetric cyclization leading to optically active Wieland-Miescher ketone analogue has been developed employing D-phenylalanine and D-CSA in [hmim]PF6 and dimethylimidazolidinone in 81% chemical yield and 74% enantiomeric excess in average after five uses. A Hajos-Wiechert ketone analogue was also synthesized in a similar manner.

    DOI: 10.1055/s-2007-970740

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  • The first total synthesis of (+)-(Z)-laureatin

    Masashi Sugimoto, Toshio Suzuki, Hisahiro Hagiwara, Takashi Hoshi

    TETRAHEDRON LETTERS   48 ( 7 )   1109 - 1112   2007年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    The stereoselective total synthesis of (+)-(Z)-laureatin is described. The 3,8-dioxabicyclo[5.1.1]nonane skeleton possessing trans-orientated alkyl substituents at the alpha,alpha'-positions to the ether linkage was stereoselectively constructed via formation of the oxetane arising from 4-exo cyclization of hydroxy epoxide existing on the oxocene core. (c) 2006 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2006.12.082

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  • Total synthesis of (-)-12,13-epi-obtusenyne

    Toshio Suzuki, Nobuyuki Yoshino, Toshiyuki Uemura, Hisahiro Hagiwara, Takashi Hoshi

    CHEMISTRY LETTERS   36 ( 2 )   278 - 279   2007年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    The stereoselective total synthesis of (-)-12,13-epi-obtusenyne is described. The oxonene skeleton possessing cis-orientated alkyl substituents at the alpha,alpha'-positions to ether linkage was stereoselectively constructed via cyclization of the corresponding hydroxy epoxide promoted by Eu(fod)(3).

    DOI: 10.1246/cl.2007.278

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  • Total synthesis of (+)-obtusenyne

    Toshiyuki Uemura, Toshio Suzuki, Naohiro Onodera, Hisahiro Hagiwara, Takashi Hoshi

    TETRAHEDRON LETTERS   48 ( 4 )   715 - 719   2007年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    The stercoselective total synthesis of (+)-obtusenyne is described. The oxonene skeleton possessing trans-orientated alkyl substituents at the alpha,alpha'-positions was stereoselectively constructed via cyclization of the corresponding hydroxy epoxide promoted by Eu(fod)(3). (c) 2006 Published by Elsevier Ltd.

    DOI: 10.1016/j.tetlet.2006.11.080

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  • Supported ionic liquid catalyst (Pd-SILC) for highly efficient and recyclable Suzuki-Miyaura reaction

    Hisahiro Hagiwara, Keon Hyeok Ko, Takashi Hoshi, Toshio Suzuki

    CHEMICAL COMMUNICATIONS   ( 27 )   2838 - 2840   2007年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    Highly efficient Suzuki-Miyaura coupling of aryl halides with arylboronic acid was realized in 50% aqueous ethanol at room temperature employing Pd(OAc)(2) immobilized in diethylaminopropylated (NDEAP) alumina pores with the aid of [bmim]PF6, which enabled recycle use up to five times in 95% average yield and turnover number of two million.

    DOI: 10.1039/b704098a

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  • The first example of samarium diiodide-promoted intramolecular ketone-ester coupling of ketones tethering acyloxyalkyl side chains producing 2-hydroxy cyclic hemiacetals

    Eietsu Hasegawa, Kentaro Okamoto, Naoko Tanikawa, Momoe Nakamura, Kazuki Iwaya, Takashi Hoshi, Toshio Suzuki

    TETRAHEDRON LETTERS   47 ( 44 )   7715 - 7718   2006年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    The reaction of samarium diiodide with some cyclic and acyclic ketones tethering acyloxyalkyl side chains produced 2-hydroxy cyclic hemiacetals in moderate to good yields, in which an intramolecular addition of samarium ketyl radicals to distant ester carbonyls would be involved. (c) 2006 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2006.08.126

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  • Heterogeneous amine catalyst grafted on amorphous silica: An effective organocatalyst for microwave-promoted Michael reaction of 1,3-dicarbonyl compounds in water

    Hisahiro Hagiwara, Sachiyo Inotsume, Masakazu Fukushima, Takashi Hoshi, Toshio Suzuki

    CHEMISTRY LETTERS   35 ( 8 )   926 - 927   2006年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    Michael addition of a 1,3-dicarbonyl compound to an alpha,beta-unsaturated carbonyl compound was effectively catalyzed by heterogeneous N,N-diethylaminopropylated silica gel (NDEAP) in water under microwave heating. The reaction condition was mild, practical, and environmentally benign. The sustainable nature of the catalyst was exemplified by re-use up to 5 times.

    DOI: 10.1246/cl.2006.926

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  • Practical aldol reaction of trimethylsilyl enolate with aldehyde catalyzed by N-methylimidazole as a Lewis base catalyst

    Hisahiro Hagiwara, Hideyuki Inoguchi, Masakazu Fukushima, Takashi Hoshi, Toshio Suzuki

    TETRAHEDRON LETTERS   47 ( 30 )   5371 - 5373   2006年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Aldol reaction of trimethylsilyl enolate with aldehyde proceeded in the presence of a catalytic amount of a Lewis base, N-methylimidazole, and lithium chloride in DMF at room temperature. Not only aryl aldehyde but also alkyl aldehyde provided the aldol product in satisfactory yields. The reaction was mild enough to apply to the aldehyde having HO, AcO, THPO, TBDMSO, MeS, pyridyl or olefinic group. Microwave irradiation accelerated the reaction. (c) 2006 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2006.05.074

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  • Synthetic transformation of ptychantin into forskolin and 1,9-dideoxyforskolin

    Hisahiro Hagiwara, Fumihide Takeuchi, Masaru Kudou, Takashi Hoshi, Toshio Suzuki, Toshihiro Hashimoto, Yoshinori Asakawa

    JOURNAL OF ORGANIC CHEMISTRY   71 ( 12 )   4619 - 4624   2006年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Forskolin ( 1), a highly oxygenated labdane diterpenoid and an activator of adenylate cyclase, has been synthesized in 12 steps and 12% overall yield from ptychantin A (4), which has been isolated from liverwort Ptychanthus striatus in good yield. The 1 alpha-hydroxy group was furnished by stereoselective reduction of the corresponding carbonyl group by sodium in t-BuOH. The 9 alpha-hydroxy group was introduced stereoselectively by epoxidation of Delta(9.11)-enolether. 1,9-Dideoxyforskolin (2), an inhibitor of glucose transporter, has been synthesized in 8 steps and 37% overall yield. The hydroxy group at C-1 was removed by solid-state thicarbonylimidazolation and subsequent radical cleavage.

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  • Sequential Knoevenagel reaction/Mislow-Evans rearrangement catalyzed by heterogeneous amine grafted on silica in water, leading to γ-hydroxy- α,β-unsaturated nitrile

    Hisahiro Hagiwara, Kohei Isobe, Ayuko Numamae, Takashi Hoshi, Toshio Suzuki

    Synlett   ( 10 )   1601 - 1603   2006年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    γ-Hydroxy-α,β-unsaturated nitrile was obtained by the reaction of α-arylsulfinylacetonitrile with aldehyde in water, which was catalyzed by N,N-diethylaminopropylated silica gel. The overall transformation proceeded via five sequential reactions, 1,2-addition of acetonitrile, dehydration (Knoevenagel condensation), isomerization of the double bond, rearrangement of sulfinyl group (Mislow-Evans rearrangement) and hydrolysis of sulfinyl ester. The reaction condition was mild such that the AcO, TBMDSO or OTHP group remained intact in the products. ? Georg Thieme Verlag Stuttgart.

    DOI: 10.1055/s-2006-941590

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  • Microwave-promoted sequential three-component synthesis of tetrahydrobenzo[b]pyran in water catlyzed by heterogeneous amine grafted on silica

    Hisahiro Hagiwara, Ayuko Numamae, Kohei Isobe, Takashi Hoshi, Toshio Suzuki

    HETEROCYCLES   68 ( 5 )   889 - 895   2006年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    A variety of tetrahydrobenzo[b]pyrans have been synthesized by sequential addition of arylaldehydes, cyanoacetate and then dimedone in water under microwave irradiation. A heterogeneous amine, N,N-diethylamino-propylated silica, was an effective catalyst for the reaction. The reaction with malononitrile provided the same result. The reaction condition was general to apply to the aldehyde having a Cl, NO2, OH, OMe, or CO2H group in satisfactory yield.

    DOI: 10.3987/COM-06-10698

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  • Immobilization of Pd(OAc)(2) in ionic liquid on silica: Application to sustainable Mizoroki-Heck reaction (vol 6, pg 2327, 2004)

    H Hagiwara, Y Sugawara, K Isobe, T Hoshi, T Suzuki

    ORGANIC LETTERS   8 ( 8 )   1749 - 1749   2006年4月

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    記述言語:英語   出版者・発行元:AMER CHEMICAL SOC  

    DOI: 10.1021/ol060525h

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  • Erratum: Sustainable Mizoroki-Heck reaction in water: Remarkably high activity of Pd(OAc)<inf>2</inf>immobilized on reversed phase silica gel with the aid of an ionic liquid (Chemical Communications (2005) (2942-2944) DOI:10.1039/b502528a)

    Hisahiro Hagiwara, Yoshitaka Sugawara, Takashi Hoshi, Toshio Suzuki

    Chemical Communications   1334   2006年3月

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  • Knoevenagel reaction in water catalyzed by amine supported on silica gel

    Kohei Isobe, Takashi Hoshi, Toshio Suzuki, Hisahiro Hagiwara

    MOLECULAR DIVERSITY   9 ( 4 )   317 - 320   2005年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:SPRINGER  

    An environmentally benign and sustainable Knoevenagel reaction of aldehyde with ethyl cyanoacetate has been achieved at ambient temperature in water employing 3-aminopropylated silica gel (NAP) as a catalyst. Wide applicability of the reaction is illustrated by the results that not only arylaldehydes of both electronic characters but also aliphatic aldehydes afforded the products. The reaction condition was so mild that aldehydes having acid- or base-sensitive substituents provided substituted alpha-cyano-alpha, beta-unsaturated esters. The catalyst has been efficiently recycled more than five times without any pre-treatment. Catalyst loading was successfully reduced to 0.0029 mmol% (TON = up to 9,226). This protocol was also applicable to the Knoevenagel reaction of malononitrile in good yields in water.

    DOI: 10.1007/s11030-005-8107-0

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  • Enantiomerically pure 2-bromo-2′-diphenylphosphinyl-1,1′- binaphthyl as a monophosphorus template for electrophilic functionalization in chiral MOP-type ligand synthesis

    Takashi Hoshi, Tetsuji Hayakawa, Toshio Suzuki, Hisahiro Hagiwara

    Journal of Organic Chemistry   70 ( 22 )   9085 - 9087   2005年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    Pd-catalyzed monophosphinylation of (R)-2-bromo-2′-iodo-1,1′- binaphthyl with Ph2P(O)H afforded (R)-2-bromo-2′- diphenylphosphinyl-1,1′-binaphthyl in good yield with excellent chemoselectivity and no observable racemization. Subsequent lithiation in the presence of excess thiosulfonate furnished an enantiomerically pure sulfenylation product, which was reduced to afford a chiral S-MOP ligand. ? 2005 American Chemical Society.

    DOI: 10.1021/jo051581j

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  • Aldol reaction of trimethylsilyl enolate with aldehyde catalyzed by pyridine N-oxide as a Lewis base catalyst

    H Hagiwara, H Inoguchi, M Fukushima, T Hoshi, T Suzuki

    SYNLETT   ( 15 )   2388 - 2390   2005年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:GEORG THIEME VERLAG KG  

    Aldol reaction of trimethylsilyl enolate with aldehydes proceeded in the presence of a catalytic amount of a Lewis base, pyridine N-oxide, and lithium chloride in DMF at room temperature. Not only aryl aldehydes but also alkyl aldehydes provided the aldol products in satisfactory yields. The reaction was mild enough to apply to aldehydes having HO, AcO, THPO, TBDMSO, MeS, pyridyl, or olefinic groups.

    DOI: 10.1055/s-2005-872664

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  • Sustainable domino Michael reaction catalyzed by a Bronsted base on silica gel: synthesis of bicyclo[2.2.2]octane-2,5-dione derivatives

    M Fukushima, S Endou, T Hoshi, T Suzuki, H Hagiwara

    TETRAHEDRON LETTERS   46 ( 19 )   3287 - 3290   2005年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Domino Michael reactions of oxophorone and its derivatives 4 with Michael partners 3 have been effected to give bicyclo[2.2.2]octane-2,5-dione derivatives 7 by a catalytic amount of a Bronsted base (NMAP-Li) generated from N-methylaminopropylated silica gel (NMAP) and n-BuLi. The NMAP pellets were efficiently reused up to six times in 86% average yield. (c) 2005 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2005.03.092

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  • The first total synthesis of (-)-methyl barbascoate

    H Hagiwara, K Hamano, M Nozawa, T Hoshi, T Suzuki, F Kido

    JOURNAL OF ORGANIC CHEMISTRY   70 ( 6 )   2250 - 2255   2005年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    The neo-trans-clerodane natural product, (-)-methyl barbascoate 1, has been synthesized for the first time starting from the known ketone 6 derived from (R)-(-)-Wieland-Miescher ketone analogue 5.

    DOI: 10.1021/jo0478499

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  • Self-aldol condensation of unmodified aldehyde in supercritical carbon dioxide catalyzed by amine grafted on silica

    H Hagiwara, J Hamaya, T Hoshi, C Yokoyama

    TETRAHEDRON LETTERS   46 ( 3 )   393 - 395   2005年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Self-aldol condensation of an unmodified aldehyde has been effected by 3-N-methylaminoprophylated silica as a catalyst in supercritical carbon dioxide, to give an alpha,beta-unsaturated aldehyde (enal). Aldehydes having acid or base-sensitive substituents provided desired enals. (C) 2004 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2004.11.120

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  • Sustainable Mizoroki-Heck reaction in water: remarkably high activity of Pd(OAc)(2) immobilized on reversed phase silica gel with the aid of an ionic liquid

    H Hagiwara, Y Sugawara, T Hoshi, T Suzuki

    CHEMICAL COMMUNICATIONS   ( 23 )   2942 - 2944   2005年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    Palladium acetate immobilized on reversed phase amorphous silica gel with the aid of an ionic liquid, [bmim]PF6, was highly efficient in the promotion of the Mizoroki - Heck reaction in pure water without a ligand up to the sixth re-use, in 95% average yield with TON and TOF 1,600,000 and 71,000 (h(-1)), respectively.

    DOI: 10.1039/b502528a

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  • Sustainable transesterification of β-ketoesters catalyzed by amine grafted on silica gel

    Hisahiro Hagiwara, Aiko Koseki, Kohei Isobe, Ken Ichi Shimizu, Takashi Hoshi, Toshio Suzuki

    Synlett   ( 12 )   2188 - 2190   2004年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    Transesterification of β-ketoesters with various alcohols has been effected by N,N-diethylaminopropylated silica gel (NDEAP) as a catalyst in refluxing xylene. Generality of the reaction was demonstrated by successful transesterification of olefinic alcohols, tertiary alcohols and alcohols having acid- or base-sensitive substituents. The catalyst has been efficiently recycled more than five times without any re-activation.

    DOI: 10.1055/s-2004-831309

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  • Immobilization of Pd(OAc)(2) in ionic liquid on silica: Application to sustainable Mizoroki-Heck reaction

    H Hagiwara, Y Sugawara, K Isobe, T Hoshi, T Suzuki

    ORGANIC LETTERS   6 ( 14 )   2325 - 2328   2004年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Palladium acetate was supported on amorphous silica with the aid of an ionic liquid, [bmim]PF6. The immobilized catalyst was highly efficient in promoting the Mizoroki-Heck reaction without a ligand in n-dodecane for at least six reuses, in 89-98% yields. The TON and TOF reached 68 400 and 8000, respectively.

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  • Catalytic asymmetric 1,4-conjugate addition of unmodified aldehyde in ionic liquid

    H Hagiwara, T Okabe, T Hoshi, T Suzuki

    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL   214 ( 1 )   167 - 174   2004年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ELSEVIER SCIENCE BV  

    In the presence of a catalytic amount of optically active pyrrolidine derivatives derived from L-proline, conjugate addition of an unmodified aldehyde to 3-buten-2-one in [bmim]PF(6) was achieved to afford (2S)-5-keto-aldehyde in up to 59% ee. (C) 2004 Elsevier B.V. All rights reserved.

    DOI: 10.1016/j.molcata.2003.11.035

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  • Resolution-free route to chiral 2,2′-bis(pyridin-2-yl)-1,1′- binaphthyl ligand: Photochemical CpCo(CO)<inf>2</inf>-mediated cycloaddition of enantiopure 2,2′-dicyano-1,1′-binaphthyl with diynes

    Takashi Hoshi, Masayoshi Katano, Eiji Nozawa, Toshio Suzuki, Hisahiro Hagiwara

    Tetrahedron Letters   45 ( 17 )   3489 - 3491   2004年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    A resolution-free route to chiral 2,2′-bis(pyridin-2-yl)- 1,1′-binaphthyl ligands 2 was developed for the first time based on the photochemical CpCo(CO)2-mediated cycloaddition reaction of enantiopure 2,2′-dicyano-1,1′-binaphthyl 3 with 1,6-heptadiyne, 1,7-octadiyne, 1,8-nonadiyne, and 2,8-decadiyne. ? 2004 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2004.02.155

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  • Practical synthetic protocols of enantiopure 1,1′-binaphthyl-2, 2′-dicarboxylic acid and 2,2′-dicyano-1,1′-binaphthyl starting from optically active dibromide precursor

    Takashi Hoshi, Eiji Nozawa, Masayoshi Katano, Toshio Suzuki, Hisahiro Hagiwara

    Tetrahedron Letters   45 ( 17 )   3485 - 3487   2004年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    Dilithiation of optically active 2,2′-dibromo-1,1′-binaphthyl 2 with t-BuLi followed by carboxylation of the resulting dilithio-intermediate 3 with CO2gave optically active 1,1′-binaphthyl-2,2′-dicarboxylic acid 1, which was further transformed to its dicyano derivative 4. Both of these transformations were carried out in a one-pot operation and the products were obtained in excellent yields with no observable racemization. ? 2004 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2004.02.156

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  • Autocatalytic domino Michael reaction leading to bicyclo[2.2.2]octane-2,5-dione derivatives

    H Hagiwara, S Endou, M Fukushima, T Hoshi, T Suzuki

    ORGANIC LETTERS   6 ( 7 )   1115 - 1118   2004年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    In the presence of a catalytic amount of lithium amide, the reaction of oxophorone with electron-deficient olefins afforded bicyclo[2.2.2]octane-2,5-dione derivatives in high yields. The reaction proceeds autocatalytically by an enolate of bicyclo[2.2.2]octane-2,5-dione, generated by an initial domino Michael reaction.

    DOI: 10.1021/ol049948e

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  • The first total synthesis and determination of the absolute configuration of chapecoderin A, B and C

    H Hagiwara, F Takeuchi, M Nozawa, T Hoshi, T Suzuki

    TETRAHEDRON   60 ( 9 )   1983 - 1989   2004年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    The seco- and rearranged-labdanes, chapecoderins A 1, B 2, and C 3 have been synthesized for the first time starting from (S)-(+)-Wieland-Miescher ketone analogue 11. Their absolute configurations have been determined as depicted in the structures 1, 2 and 3. (C) 2004 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2004.01.004

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  • An efficient alternative synthesis of (+)-(6S,7S)-7-hydroxy-6,11-cyclofarnes-3(15)-en-2-one, the (S)-enantiomer of the antibacterial sesquiterpene from Premna oligotricha

    M Nozawa, T Hoshi, T Suzuki, H Hagiwara

    SYNTHETIC COMMUNICATIONS   34 ( 1 )   187 - 195   2004年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:MARCEL DEKKER INC  

    The title compound has been synthesized from optically active lactone derived from (S)-(+)-Wieland-Miescher ketone analogue employing solid-state Baeyer-Villiger reaction.

    DOI: 10.1081/SCC-120027252

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  • Sustainable self-aldol condensation of unmodified aldehyde: A combination of ionic liquid and heterogeneous secondary-amine grafted on silica

    J Hamaya, T Suzuki, T Hoshi, K Shimizu, Y Kitayama, H Hagiwara

    SYNLETT   ( 6 )   873 - 875   2003年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:GEORG THIEME VERLAG KG  

    Self-aldol condensation of an unmodified aldehyde has been effected by N-methyl-3-aminopropylated silica as a catalyst in ionic liquid, [bmim]PF(6), to give an alpha,beta-unsaturated aldehyde (enal). Aldehydes having acid or base sensitive substituents provided desired enals in satisfactory yields. The reaction system has been efficiently recycled more than eight times.

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  • Total synthesis of (+)-laurallene

    T Saitoh, T Suzuki, M Sugimoto, H Hagiwara, T Hoshi

    TETRAHEDRON LETTERS   44 ( 15 )   3175 - 3178   2003年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    The stereoselective total synthesis of (+)-laurallene is described. The required key oxocene skeleton possessing trans-orientated alkyl substituents at the alpha,alpha'-positions was stereo selectively constructed via the cyclization of the corresponding hydroxy epoxide promoted by Eu(fod)(3). (C) 2003 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(03)00432-5

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  • First synthesis of 1,9-dideoxyforskolin from ptychantin A

    H Hagiwara, F Takeuchi, T Hoshi, T Suzuki, T Hashimoto, Y Asakawa

    TETRAHEDRON LETTERS   44 ( 11 )   2305 - 2306   2003年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    1,9-Dideoxyforskolin 2 has been synthesized starting from ptyebantin A 3. (C) 2003 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(03)00236-3

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  • Stereospecific synthesis of eight- and nine-membered cyclic ethers by Eu(fod)(3)-mediated cyclization of hydroxy epoxides

    T Saitoh, T Suzuki, N Onodera, H Sekiguchi, H Hagiwara, T Hoshi

    TETRAHEDRON LETTERS   44 ( 13 )   2709 - 2712   2003年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    An efficient and versatile method for the stereospecific construction of alpha,omega-cis- and alpha,omega-trans-disubstituted eight- and nine-membered cyclic ethers was developed. Cyclization of the hydroxy epoxides promoted by Eu(fod)(3) proceeded via an S(N)2 process and exo mode to provide the corresponding cyclic ethers in excellent yields. (C) 2003 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(03)00335-6

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  • First total synthesis of valeriananoid A

    H Hagiwara, A Morii, Y Yamada, T Hoshi, T Suzuki

    TETRAHEDRON LETTERS   44 ( 8 )   1595 - 1597   2003年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    A tricyclic sesquiterpenoid, valeriananoid A 1, has been synthesized via domino Michael reaction of oxophorone 4 and subsequent 6-endo-trig cyclization of a ketyl radical as key steps. (C) 2003 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(03)00064-9

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  • Diethylaminotrimethylsilane-catalyzed 1,4-addition of aldehydes to vinyl ketones: (3R)-3,7-dimethyl-2-(3-oxobutyl)-6-octenal: [(6-Octenal, 3,7-dimethyl-2-(3-oxobutyl)-, (3R)-)]

    Hisahiro Hagiwara, Hiroki Ono, Takashi Hoshi, Kwame Nti-Addae, Steven Wolff

    Organic Syntheses   80   195 - 199   2003年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley Blackwell  

    DOI: 10.15227/orgsyn.080.0195

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  • Syntheses and reactions of (R)-(C<inf>10</inf>H<inf>6</inf>)<inf>2</inf>M<inf>2</inf>(M=SnMeCl<inf>2</inf>, SnMe<inf>2</inf>Cl, SnMe(OTf)<inf>2</inf>, SnMe<inf>2</inf>OTf, SiMe<inf>2</inf>I) as novel chiral 2,2′-bis-metallic-1,1′-binaphthyl catalysts

    Takashi Hoshi, Hiroshi Shionoiri, Masayoshi Katano, Toshio Suzuki, Hisahiro Hagiwara

    Tetrahedron Asymmetry   13 ( 19 )   2167 - 2175   2002年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    (R)-(C10H6)2M2(M=SnMeCl2, SnMe2Cl, SnMe(OTf)2, SnMe2OTf, SiMe2I) were synthesized as novel chiral 2,2′-bis-metallic-1,1′-binaphthyl catalysts. The catalytic activities were evaluated in the Diels-Alder reaction of methacrolein and cyclopentadiene and the asymmetric acylation reaction of racemic 1-phenyl-1,2-ethanediol. ? 2002 Published by Elsevier Science Ltd.

    DOI: 10.1016/S0957-4166(02)00578-5

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  • Erratum: The first enantioselective total synthesis of cyclomyltaylane-5α-ol and determination of its absolute stereochemistry (Journal of the Chemical Society, Perkin Transactions 1 (2002) (583-591))

    Hisahiro Hagiwara, Hitoshi Sakai, Takashi Uchiyama, Yoshiaki Ito, Noriyuki Morita, Takashi Hoshi, Toshio Suzuki, Masayoshi Ando

    Journal of the Chemical Society. Perkin Transactions 1   1920   2002年9月

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  • Domino ring opening-ring closing metathesis (ROM-RCM) strategy toward bicyclo[n.3.0]cycloalkenes

    H Hagiwara, T Katsumi, S Endou, T Hoshi, T Suzuki

    TETRAHEDRON   58 ( 33 )   6651 - 6654   2002年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Treatment of bicyclo[2.2.1]heptene having an exo- or endo-olefinic side chain with a catalytic amount of Grubbs' Ru carbene complex under ethylene atmosphere provided bicyclo[3.3.0]octene or bicyclo[4.3.0]nonene compounds by domino ROM-RCM reaction. (C) 2002 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4020(02)00690-7

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  • First total syntheses of the phytotoxins solanapyrones D and E via the domino Michael protocol

    H Hagiwara, K Kobayashi, S Miya, T Hoshi, T Suzuki, M Ando, T Okamoto, M Kobayashi, Yamamoto, I, S Ohtsubo, M Kato, H Uda

    JOURNAL OF ORGANIC CHEMISTRY   67 ( 17 )   5969 - 5976   2002年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    The phytotoxins solanapyrones D (1) and E (2) have been synthesized from the decalone prepared by the domino Michael reaction of the kinetic enolate of optically pure acetylcyclohexene with methyl crotonate. The decalone was transformed into a solanapyrone core by equilibration into thermodynamically stable trans-decalone (11), dehydroxylation, and dehydration. Condensation of a methyl acetoacetate equivalent followed by cyclization installed a pyrone moiety. Introduction of a formyl or hydroxymethyl unit into the pyrone ring via Pummerer related reactions furnished solanapyrones D (1) and E (2).

    DOI: 10.1021/jo0163602

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  • (R)-2,2′-bis(stannyl)-1,1′-binaphthyls as a new chiral bis-metallic binaphthyl catalyst

    Takashi Hoshi, Hiroshi Shionoiri, Masayoshi Katano, Toshio Suzuki, Masayoshi Ando, Hisahiro Hagiwara

    Chemistry Letters   ( 6 )   600 - 601   2002年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    Dilithiation followed by bis-stannylation with Me3SnCl of (R)-2,2′-dibromo-1,1′-binaphthyl (2) and the subsequent redistribution reaction of resulting (R)-2,2′-bis(trimethylstannyl)-1,1′-binaphthyl (6) with SnCl4 gave the novel chiral Lewis acid catalyst (R)-2,2′-bis(dichloromethylstannyl)-1,1′-binaphthyl (4). The catalytic properties of 4 and its triflate 5 were investigated as the first chiral bis-metallic binaphthyl catalyst.

    DOI: 10.1246/cl.2002.600

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  • Conjugate addition of unmodified aldehydes: recycle of heterogeneous amine catalyst and ionic liquid

    H Hagiwara, T Sayuri, T Okabe, T Hoshi, T Suzuki, H Suzuki, K Shimizu, Y Kitayama

    GREEN CHEMISTRY   4 ( 5 )   461 - 463   2002年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    Unmodified aldehydes add to vinylketones in 1,4-manner in ionic liquid, [bmim]PF(6), in the presence of a catalytic amount of propylamine grafted on silica. The ionic liquid involving the catalyst has been recycled intact without loss of efficiency.

    DOI: 10.1039/b201900k

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  • The first enantioselective total synthesis of cyclomyltaylane-5α-ol and determination of its absolute stereochemistry

    Hisahiro Hagiwara, Hitoshi Sakai, Takashi Uchiyama, Yoshiaki Ito, Noriyuki Morita, Takashi Hoshi, Toshio Suzuki, Masayoshi Ando

    Journal of the Chemical Society. Perkin Transactions 1   2 ( 5 )   583 - 591   2002年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    The tetracyclic sesquiterpenoid (+)-cyclomyltaylan-5α-ol 1 has been synthesized starting from (S)-(+)-Hajos?Wiechert ketone analogue 10 via stereoselective Claisen rearrangement followed by SmI2-promoted reductive cyclisation. Thus, the absolute configuration has been established to be 2R,3R,4R,5S,6R,7R (cyclomyltaylane numbering) as depicted in structure 1. ? 2002 The Royal Society of Chemistry.

    DOI: 10.1039/b111594b

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  • The creation of a database of odorous compounds focused on molecular rigidity and analysis of the molecular features of the compounds in the database

    Fumiko Yoshii, Yoshiaki Yamada, Takashi Hoshi, Hisahiro Hagiwara

    Chemical Senses   27 ( 5 )   399 - 405   2002年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    It is important to select odorous molecules for experiments on olfaction and for the development of an electronic nose. Odorous molecules having a small number of conformers, namely structurally rigid molecules, are assumed to interact with a small number of types of olfactory receptor proteins or to interact with the proteins in a simpler manner than that of fairly flexible molecules. Focusing on the rigidity of molecular structures, we collected 287 odorous molecules from data sources, which included 1205 chemicals in total and a database of the 287 odorous molecules (DB⊙MOL) was created using CS ChemFinder Pro (version 5.0). The logarithmic value of the octanol/water partition coefficient (log P) and melting point, boiling point and vapour pressure of the molecules were estimated using CS Chem3D Pro. The database DB⊙MOL accumulates these estimated data in addition to literature values for odour quality, odour detection thresholds and the safety of molecules. The rigidity of the 287 molecules was further analysed by conformational analysis performed by molecular mechanics using Conformer® in CS Chem3D Pro (version 5) and 72 rigid odorous molecules were selected. The 287 molecules were also analysed based on atomic composition, substructure and molecular size. Sixty-two odorous molecules among the 72 rigid odorous molecules were further selected based on their atomic composition. The 62 rigid molecules with simple atomic composition that were finally selected should be useful for researchers in choosing odorous molecules for the study of olfaction, including the fields of molecular biology, physiology, structure-odour relationships and other fields of the study concerning odour.

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  • Total synthesis of bisabolane sesquiterpenoids, α-bisabol-1-one, curcumene, curcuphenol and elvirol: Utility of catalytic enamine reaction in cyclohexenone synthesis

    Hisahiro Hagiwara, Tomoyuki Okabe, Hiroki Ono, Vijayendra P. Kamat, Takashi Hoshi, Toshio Suzuki, Masayoshi Ando

    Journal of the Chemical Society. Perkin Transactions 1   2 ( 7 )   895 - 900   2002年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    Total syntheses of α-bisabol-1-one, curcumene, curcuphenol and elvirol have been accomplished via 1,4-conjugate addition of intact aldehydes to vinyl ketones followed by an intramolecular aldol condensation. ? 2002 The Royal Society of Chemistry.

    DOI: 10.1039/b200629b

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  • First total synthesis of chapecoderin A: absolute configuration of the natural product

    H Hagiwara, F Takeuchi, T Hoshi, T Suzuki, M Ando

    TETRAHEDRON LETTERS   42 ( 43 )   7629 - 7631   2001年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    A seco-labdane, chapecoderin A 1, has been synthesized starting from (S)-(+)-Wieland-Miescher ketone analogue 9. The absolute configuration has been determined to be 55,10S. (C) 2001 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(01)01647-1

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  • Heterogeneous Heck reaction catalyzed by Pd/C in ionic liquid

    H Hagiwara, Y Shimizu, T Hoshi, T Suzuki, M Ando, K Ohkubo, C Yokoyama

    TETRAHEDRON LETTERS   42 ( 26 )   4349 - 4351   2001年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Pd/C-catalyzed Heck reactions of aryl halides with olefins proceeded in moderate to satisfactory yields in ionic liquid [bmim]PF(6). The ionic liquid involving a catalyst was easily recycled. (C) 2001 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(01)00748-1

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  • A new protocol for synthesis of 3-hydroxymethyl-4-methoxy-2H-pyrone derivatives

    H Hagiwara, K Kobayashi, T Hoshi, T Suzuki, M Ando

    TETRAHEDRON   57 ( 24 )   5039 - 5043   2001年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    The title compounds have been prepared by treatment of 4-methoxy-3-phenylsulfinylmethyl-2H-pyrone derivatives with trifluoroacetic anhydride, followed by basic work-up. (C) 2001 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4020(01)00347-7

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  • Catalytic enamine reaction: an expedient 1,4-conjugate addition of naked aldehydes to vinylketones and its application to synthesis of cyclohexenone from Stevia purpurea

    H Hagiwara, T Okabe, K Hakoda, T Hoshi, H Ono, VP Kamat, T Suzuki, M Ando

    TETRAHEDRON LETTERS   42 ( 14 )   2705 - 2707   2001年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Naked aldehydes directly add in a 1,4-manner to vinylketones in the presence of 0.2 equiv. of diethylamine in sealed tubes to provide 5-keto aldehydes. (C) 2001 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(01)00247-7

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  • The first total synthesis of (+)-rogioloxepane A

    R Matsumura, T Suzuki, H Hagiwara, T Hoshi, M Ando

    TETRAHEDRON LETTERS   42 ( 8 )   1543 - 1546   2001年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    The first total synthesis of (+)-rogioloxepane A is described. The alpha,omega -trans-disubstituted oxepene skeleton was stereoselectively constructed via cyclization of the hydroxy epoxide promoted by the (Bu3Sn)(2)O/Zn(OTf)(2) system. The proposed configurations of 6R and 13R were confirmed through this synthetic study. (C) 2001 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(00)02281-4

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  • Formal synthesis of (+)-isolaurepinnacin

    T Suzuki, R Matsumura, K Oku, K Taguchi, H Hagiwara, T Hoshi, M Ando

    TETRAHEDRON LETTERS   42 ( 1 )   65 - 67   2001年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    The stereoselective formal synthesis of (+)-isolaurepinnacin is described. The required key oxepene skeleton possessing cis-oriented alkyl substituents at the alpha,omega -positions was stereoselectively constructed via the cyclization of the corresponding hydroxy epoxide promoted by the (Bu3Sn)(2)O/Zn(OTf)(2) system. (C) 2000 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(00)01880-3

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  • The first total synthesis of (-)-solanapyrone E based on domino Michael strategy

    H Hagiwara, K Kobayashi, S Miya, T Hoshi, T Suzuki, M Ando

    ORGANIC LETTERS   3 ( 2 )   251 - 254   2001年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    [GRAPHICS]
    A phytotoxin, solanapyrone E, has been synthesized from the decalone prepared by the domino Michael reaction of the kinetic enolate of optically pure acetylcyclohexene with methyl crotonate, After several transformations on the decalone ring, condensation of a methyl acetoacetate equivalent installed a pyrone moiety and introduction of a hydroxymethyl unit into the pyrone ring furnished solanapyrone E.

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  • Domino Michael-O-alkylation reaction: one-pot synthesis of 2,4-diacylhydrofuran derivatives and its application to antitumor naphthofuran synthesis

    H Hagiwara, K Sato, D Nishino, T Hoshi, T Suzuki, M Ando

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   1 ( 22 )   2946 - 2957   2001年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    The reaction of enolates of 1,3-dicarbonyl compounds with alpha -halo-alpha, beta -unsaturated carbonyl compounds affords 2,4-diacyldihydrofuran derivatives in the presence of DBU in THF. Chemical manganese dioxide oxidation of the hydrofurans leads to 2,4-diacylfuran derivatives. Application of the protocol enables short-step syntheses of antitumor naphthofuran natural products.

    DOI: 10.1039/b107180g

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  • Diethylamino(trimethyl)silane-mediated direct 1,4-addition of naked aldehydes to electron-deficient olefins

    H Hagiwara, N Komatsubara, H Ono, T Okabe, T Hoshi, T Suzuki, M Ando, M Kato

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 3 )   316 - 322   2001年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    Aldehydes directly add in a 1,4-manner to electron-deficient olefins in the presence of diethylamino(trimethyl)silane.

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  • Conformational analysis and selection of odor-active conformers: Synthesis of molecules designed for the Lily-of-the-Valley(Muguet)-type odor

    F Yoshii, T Nakamura, S Hirono, Y Shimizu, T Hoshi, M Ando, H Hagiwara

    HELVETICA CHIMICA ACTA   84 ( 7 )   2051 - 2063   2001年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY-V C H VERLAG GMBH  

    The selection of odor-active conformers and the construction of a model for a targeted odor type, i.e., for the lily-of-the-valley odor, were examined. The disagreement of the odors of 1,3,4,5-tetrahydro-2-benzoxepin derivative 1 and 3-[4-(tert-butyl)phenyl]-2-methylpropanal (2) is discussed in terms of their stable conformers. The conformer active for the lily-of-the-valley odor was investigated by conformational analyses of several related compounds. Based on the integrated model consisting of the assumed active conformers (Fig. 5), compounds anticipated to possess the lily-of-the-valley odor were designed and synthesized. The odor of synthetic 7-(tert-butyl)-1,2,4,5-tetrahydro-3H-benzocyclohepten-3-one (8) and 3-[4-(tert-butyl)phenyl]cyclopentanone (13) were evaluated by perfumer, to have a floral odor and to recall the lily-of-the-valley anti lilac odors, respectively. Our methodology to design new odoriferous compounds. based on conformational analysis, selection of odor-active conformers, and construction of a model, proved to be satisfactory.

    DOI: 10.1002/1522-2675(20010711)84:7<2051::AID-HLCA2051>3.0.CO;2-H

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  • First C-2 symmetrical siloles: Synthetic, structural, and photophysical studies of 7-Sila-7H-dibenzo [c,g]fluorenes

    T Hoshi, T Nakamura, T Suzuki, M Ando, H Hagiwara

    ORGANOMETALLICS   19 ( 22 )   4483 - 4487   2000年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    The syntheses of 7-sila-7H-dibenzo[c,g]fluorenes 1 were effected via dilithiation of 2,2'-dibromo-1,1'-binaphthyl (2) followed by cyclization of the resulting dianion with dihalosilanes: Me2SiCl2, Ph2SiCl2, and Ph2SiF2. The X-ray structural analysis of 7-sila-7, 7-diphenyl-7N-dibenzo[c,g]fluorene (1b) provided the first geometrical parameters of the 7-sila-7H-dibenzo[c,g]fluorene derivative in which the silole skeleton was found to be twisted in the C-2 symmetrical conformation due to the significant steric repulsion of the binaphthyl group fixed within the van der Waals radii. The photophysical study and semiempirical PM3 calculation suggested the presence of significant sigma*-pi* conjugation in the LUMO of the 7-sila-7N-dibenzo[c,g]fluorene 1 like a silole.

    DOI: 10.1021/om000436n

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  • Application of ring closing metathesis to the first total synthesis of (R)-(+)-muscopyridine: Determination of absolute stereochemistry

    H Hagiwara, T Katsumi, VP Kamat, T Hoshi, T Suzuki, M Ando

    JOURNAL OF ORGANIC CHEMISTRY   65 ( 21 )   7231 - 7234   2000年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    DOI: 10.1021/jo000785r

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  • Stereospecific synthesis of α,ω-cis- and α,ω-trans-disubstituted oxepanes

    Ryuji Matsumura, Toshio Suzuki, Kohki Sato, Takashi Inotsume, Hisahiro Hagiwara, Takashi Hoshi, Vijayendra P. Kamat, Masayoshi Ando

    Tetrahedron Letters   41 ( 40 )   7697 - 7700   2000年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    An efficient and versatile method for the stereospecific construction of α,ω-cis- and α,ω-trans-disubstituted oxepane skeletons is described. Cyclization of the hydroxy epoxides promoted by a (Bu3Sn)2O/ Zn(OTf)2system proceeded via an S(N)2 process and exo mode selectivity regardless of the configuration of the hydroxyl and the epoxy groups to provide the corresponding oxepanes in excellent yields. (C) 2000 Elsevier Science Ltd.

    DOI: 10.1016/S0040-4039(00)01344-7

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  • Cyclization of hydroxy epoxides promoted by (Bu3Sn)(2)O/Lewis acid: efficient synthesis of oxepanes

    R Matsumura, T Suzuki, K Sato, K Oku, H Hagiwara, T Hoshi, M Ando, VP Kamat

    TETRAHEDRON LETTERS   41 ( 40 )   7701 - 7704   2000年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Cyclization of hydroxy epoxides mediated by a (Bu3Sn)(2)O/Lewis acid system proceeded via an S(N)2 process and exo mode to provide the corresponding seven-membered cyclic ethers in high yield. (C) 2000 Elsevier science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(00)01345-9

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  • First isolation and full characterization of 2,2′-bishalosilyl-substituted 1,1′-binaphthyls: synthesis of 2,2′-bis(fluorodimethylsilyl)-1,1′-binaphthyl and X-ray structural analysis of highly strained disilanylene-bridged precursors

    Takashi Hoshi, Tomonobu Nakamura, Toshio Suzuki, Masayoshi Ando, Hisahiro Hagiwara

    Organometallics   19 ( 16 )   3170 - 3178   2000年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    Brominative Si-Si cleavage of 3,4-disila-3,3,4,4-tetramethyl-3,4-dihydrodibenzo[c,g]-phenanthrene (3a), LiAlH4reduction of the resulting dibromide, and fluorination of the dihydride 14a thus gave 2,2′-bis(fluorodimethylsilyl)-1,1′-binaphthyl (7a) in high yield as the first isolated and fully characterized 2,2′-bis(halosilyl)-1,1′-binaphthyl. Similar conversion of the more sterically hindered 3,4-disila-3,3-dimethyl-4,4-diphenyl-3,4-dihydrodibenzo[c,g]-phenanthrene (3b) also gave the corresponding bishydrosilane 14b. However, subsequent fluorination did not give the desired bisfluorosilane 7b but rather the hydrolyzed siloxane 6b. The syntheses of the disilanylene-bridged precursors 3 were effected via bis-silylation reactions of 2,2′-dibromo-1,1′-binaphthyl (DBBN, 2) with dihalodisilanes ClMe2SiSiMe2Cl, ClMe2SiSiPh2Cl, FMe2SiSiPh2F, and FPh2SiSiPh2F. Although ClMe2SiSiMe2Cl predominately gave the disilanylene-bridged product 3a, XMe2SiSiPh2X (X = F, Cl) produced not only the disilanylene-bridged product 3b but also the dimethylsilylene-bridged product 8a. FMe2-SiSiPh2F served better in preparation of the desired 3b than ClMe2SiSiPh2Cl. The sterically hindered FPh2SiSiPh2F did not give silylation products. The X-ray structural analyses of 3a and 3b provided the first geometrical parameters of the 2,2′-disilanylene-bridged 1,1′-binaphthyl derivatives. In comparison with the acyclic analogues and less sterically hindered disilanylene-bridged biaryls such as 2,2′-bis(trimethylsilyl)-1,1′-binaphthyl ((±)-1a), (R)-(-)-2,2′-bis(dimethylphenylsilyl)-1,1′-binaphthyl ((R)-(-)-1b), dibenzo-1,1,2,2-tetramethyl-1,2-disilacyclohexa-3,5-diene (12), and dithienodisilacyclohexadiene 13 the disilanylene-bridged binaphthyls 3 were found to be highly strained due to the steric repulsion of the binaphthyl groups fixed in a narrow angle. ? 2000 American Chemical Society.

    DOI: 10.1021/om0001523

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  • Ring closing metathesis directed synthesis of (R)-(-)-Muscone from (+)-Citronellal

    VP Kamat, H Hagiwara, T Katsumi, T Hoshi, T Suzuki, M Ando

    TETRAHEDRON   56 ( 26 )   4397 - 4403   2000年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    A concise and simple synthesis of the valuable perfumery ingredient (R)-(-)-muscone 1 has been achieved through ring closing olefin metathesis (RCM) aided macrocyclization protocol as the key step. Commercially available starting material (R)-(+)-citronellal 3 has been employed as a building unit in preparing the acyclic diolefinic substrate 16, which in turn was exposed to bis(tricyclohexylphosphine)benzylideneruthenium dichloride catalyst 2 to afford the cyclic RCM reaction product 17 in 78% yield. Catalytic hydrogenation of 17 furnished enantiomerically pure (R)-(-)-muscone 1. (C) 2000 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4020(00)00333-1

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  • Bisannelation with vinylselenoxide: Synthesis of tricyclo[3.2.1.0(2,7)] octane-6-one and its congeners

    H Hagiwara, H Sakai, M Kirita, T Hoshi, T Suzuki, M Ando

    TETRAHEDRON   56 ( 11 )   1445 - 1449   2000年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Reaction of kinetic enolate of alpha'-substituted cyclohexenone derivatives with vinylselenoxides provided tricyclo[3.2.1.0(2.7)]-octane-6-one derivatives via domino Michael-Michael-substitution protocol. (C) 2000 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4020(00)00032-6

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  • Total synthesis of a monocyclofarnesane dinorsesquiterpenoid isolated from mushroom ingested by beetle: Selectivity in solid-state Baeyer-Villiger reaction

    H Hagiwara, H Nagatomo, F Yoshii, T Hoshi, T Suzuki, M Ando

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 16 )   2645 - 2648   2000年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    Dinorsesquiterpenoid 1 is synthesised starting from (S)-(+)-Wieland-Miescher ketone analogue 5 via solid-state Baeyer-Villiger reaction as a key step.

    DOI: 10.1039/b003571h

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  • Domino Michael-seleno Pummerer type reaction (additive seleno Pummerer reaction)

    H Hagiwara, K Kafuku, H Sakai, M Kirita, T Hoshi, T Suzuki, M Ando

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 16 )   2577 - 2578   2000年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    Domino Michael-seleno Pummerer type reaction (additive seleno Pummerer type rearrangement) has been realised by the reaction of 1,3-dicarbonyl compounds with vinyl selenoxides in the presence of amine and chlorosilane.

    DOI: 10.1039/b004912n

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  • Diethylaminotrimethylsilane mediated aldol condensation of naked aldehydes

    H Hagiwara, H Ono, N Komatsubara, T Hoshi, T Suzuki, M Ando

    TETRAHEDRON LETTERS   40 ( 36 )   6627 - 6630   1999年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Self-aldol condensation of naked aldehydes in the presence of diethylaminotrimethyl-silane with or without solvent provided unsaturated aldehydes. (C) 1999 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(99)01326-X

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  • Synthesis of disilacycloalkenes by ruthenium alkylidene catalyzed ring- closing metathesis (RCM) reaction of α,ω-bis(allyldimethylsilyl)- substituted compounds

    Takashi Hoshi, Hiroyuki Yasuda, Takanobu Sanji, Hideki Sakurai

    Bulletin of the Chemical Society of Japan   72 ( 4 )   821 - 827   1999年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    Ruthenium-catalyzed ring-closing metathesis (RCM) reactions of various α,ω-bis(allyldimethylsilyl)-, bis(dimethylvinylsilyl)-, and bis(dimethylvinyloxysilyl)-substituted compounds are examined. The steric and electronic influences of the substrates on the RCM reaction were discussed. AlthoUgh the successful ring-closing reactions are limited to seven-and eight-membered rings, disilacycloalkene derivatives constructed with - SiMe2-CH2-SiMe2-, -SiMe2-(CH2)2-SiMe2-, -SiMe2-O-SiMe2-, -SiMe2- N(Ph)-SiMe2-, and a vinylene unit in the ring system were obtained in good to reasonable yields under the mild reaction conditions. The limitation of the reactions is mainly ascribed to Si-C and Si-Si bonds being longer than the C-C bond in the ring system.

    DOI: 10.1246/bcsj.72.821

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  • Total synthesis of (+)-cyclomyltaylan-5α-ol isolated from the Taiwanese Liverwort Reboulia hemisphaerica

    Hitoshi Sakai, Hisahiro Hagiwara, Ito Yoshiaki, Takashi Hoshi, Toshio Suzuki, Masayoshi Ando

    Tetrahedron Letters   40 ( 15 )   2965 - 2968   1999年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    The novel tetracyclic sesquiterpenoid (+)-cyclomyltaylan-5α-ol 1 has been synthesized starting from (S)-(+)-Hajos-Wiechert ketone analogue 3 via Sml2-promoted reductive cyclization as a key step. Thus, the absolute configuration has been established to be 2R,3R,4R,5S,6R,7R (cyclomyltaylane numbering) as depicted in structure 1.

    DOI: 10.1016/S0040-4039(99)00338-X

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  • Total synthesis of a monocyclofarnesane norsesquiterpenoid isolated from mushroom ingested by beetle: utility of solid state Baeyer-Villiger oxidation

    H Hagiwara, H Nagatomo, S Kazayama, H Sakai, T Hoshi, T Suzuki, M Ando

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 4 )   457 - 459   1999年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    Norsesquiterpenoid 1 has been synthesised starting from (S)-(+)-Wieland-Miescher ketone analogue 3 via solid state Baeyer-Villiger oxidation as a key step.

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  • New access to methyl formylcyclopropanecarboxylates via diethylaminotrimethylsilane mediated tandem nucleophilic reaction of aldehyde with methyl 2,3-dihalopropanoate

    H Hagiwara, N Komatsubara, T Hoshi, T Suzuki, M Ando

    TETRAHEDRON LETTERS   40 ( 8 )   1523 - 1526   1999年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Formylcyclopropanecarboxylates have been synthesized by diethylaminotrimethylsilane mediated tandem conjugate addition-alkylation of aldehydes to methyl alpha-haloaclylate generated in situ from methyl 2,3-dihalopropanoate. (C) 1999 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(98)02668-9

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  • Methyl 2,3-dichloropropanoate as a new domino bisannelating reagent

    H Sakai, H Hagiwara, T Hoshi, T Suzuki, M Ando

    SYNTHETIC COMMUNICATIONS   29 ( 12 )   2035 - 2042   1999年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:MARCEL DEKKER INC  

    Kinetically generated enolate of cyclohexenone when reacted with methyl 2,3-dichloropropanoate provided methyl tricyclo[3.2.1.0(2,7)]octane-1-carboxylate and its congeners via domino Michael-Michael-alkylation reaction.

    DOI: 10.1080/00397919908086195

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  • Synthesis and structure of chiral (R)-2,2'-bis-silyl-substituted 1,1'-binaphthyl derivatives

    Takashi Hoshi, Hiroshi Shionoiri, Toshio Suzuki, Masayoshi Ando, Hisahiro Hagiwara

    Chemistry Letters   ( 11 )   1245 - 1246   1999年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Chemical Society of Japan  

    First synthesis of optically active 2,2'-bis-silyl-substituted 1,1'-binaphthyl derivatives, (R)-(+)-2,2'-bis(trimethylsilyl)-1,1'-binaphthyl ((R)-(+)-1) and (R)-(-)-2,2'-bis(dimethylphenylsilyl)-1,1'-binaphthyl ((R)-(-)-2), has been accomplished by the direct bis-silylation of chiral 2,2'-dibromo-1,1'-binaphthyl (DBBN). The molecular structure and the absolute configuration of (R)-(-)-2 have been determined by means of X-ray crystallography.

    DOI: 10.1246/cl.1999.1245

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  • Highly selective mono- and polyallylation of polychlorosilanes and polychlorodisilanes

    Takanobu Sanji, Mitsuhiro Iwata, Masahiro Watanabe, Takashi Hoshi, Hideki Sakurai

    Organometallics   17   5068 - 5071   1998年12月

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    The reaction of methyltrichlorosilane with an equimolar amount of allyl chloride in the presence of zinc powder proceeds quite smoothly in dimethylimidazolidinone (DMI) to give allyl(dichloro)methylsilane in high selectivity. Other RSiCl3 (R = isopropyl, tert-butyl, n-hexyl, phenyl, n-octyl, n-decyl) gave the corresponding allylated compounds, (CH2=CHCH2)-RSiCl2, highly selectively in high yield under the same conditions. Dimethyldichlorosilane and trimethylchlorosilane are also monoallylated. The reaction of 2 equiv of allyl chloride-Zn-DMI with methyltrichlorosilane gave the diallylated compound selectively. The reaction of methyltrichlorosilane with CE)-1-chloro-2-butene selectively afforded 1-methyl-2-propenyl-(methyl)dichlorosilane with allylic rearrangement. The reaction was also applied successfully to the allylation of polychlorodisilanes. ? 1998 American Chemical Society.

    DOI: 10.1021/om9805133

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  • Molecular structure and photochemical reactions of trimethylsilylmethyl-substituted masked disilene

    Takashi Hoshi, Ryusaku Shimada, Chizuko Kabuto, Takanobu Sanji, Hideki Sakurai

    Chemistry Letters   ( 5 )   427 - 428   1998年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Chemical Society of Japan  

    (Trimethylsilylmethyl)trimethyldisilene was generated photochemically from 1-phenyl-7-trimethylsilylmethyl-7,8,8-trimethyl-7,8-disilabicyclo[2.2.2]octa-2, 5-diene (masked disilene). UV spectrum and regioselectivity of the addition reaction of phenols to the disilene were discussed. The molecular structure of the masked disilene was also determined by single-crystal X-ray diffraction.

    DOI: 10.1246/cl.1998.427

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