First total synthesis of modiolide A, based on the whole-cell yeast-catalyzed asymmetric reduction of a propargyl ketone

Masaaki Matsuda; Takahiro Yamazaki; Ken ichi Fuhshuku; Takeshi Sugai

doi:10.1016/j.tet.2007.06.038

First total synthesis of modiolide A, based on the whole-cell yeast-catalyzed asymmetric reduction of a propargyl ketone

Masaaki Matsuda, Takahiro Yamazaki, Ken ichi Fuhshuku, Takeshi Sugai

薬科学科

研究成果: Article › 査読

28 被引用数 (Scopus)

抄録

While the first total synthesis of modiolide A (1a), a 10-membered ring lactone with a marine-origin was achieved, an important chiral building block for constructing the chirality at C-4 in 1a, (S)-6-[(4-methoxybenzyl)oxy]-1-trimethylsilyl-1-hexyn-3-ol (3a) was obtained in as high as 96.1% ee. Asymmetric reduction of a silylated propargyl ketone (5) mediated by whole-cell of Pichia minuta IAM 12215 was established. This yeast-mediated reduction was also applicable to provide stereochemically pure (3S,5R)-5-[(4-methoxybenzyl)oxy]-1-trimethylsilyl-1-hexyn-3-ol (15), a synthetic intermediate for the related 10-membered lactone, tuckolide (16).

本文言語	English
ページ（範囲）	8752-8760
ページ数	9
ジャーナル	Tetrahedron
巻	63
号	36
DOI	https://doi.org/10.1016/j.tet.2007.06.038
出版ステータス	Published - 2007 9 3

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

文献へのアクセス

10.1016/j.tet.2007.06.038

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引用スタイル

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title = "First total synthesis of modiolide A, based on the whole-cell yeast-catalyzed asymmetric reduction of a propargyl ketone",

abstract = "While the first total synthesis of modiolide A (1a), a 10-membered ring lactone with a marine-origin was achieved, an important chiral building block for constructing the chirality at C-4 in 1a, (S)-6-[(4-methoxybenzyl)oxy]-1-trimethylsilyl-1-hexyn-3-ol (3a) was obtained in as high as 96.1% ee. Asymmetric reduction of a silylated propargyl ketone (5) mediated by whole-cell of Pichia minuta IAM 12215 was established. This yeast-mediated reduction was also applicable to provide stereochemically pure (3S,5R)-5-[(4-methoxybenzyl)oxy]-1-trimethylsilyl-1-hexyn-3-ol (15), a synthetic intermediate for the related 10-membered lactone, tuckolide (16).",

author = "Masaaki Matsuda and Takahiro Yamazaki and Fuhshuku, {Ken ichi} and Takeshi Sugai",

note = "Funding Information: The authors thank Professor Jun-ichi Kobayashi of Hokkaido University for information on modiolide A, Professor Masatoshi Asami of Yokohama National University and Professor Keisuke Suzuki of Tokyo Institute of Technology for their valuable suggestions on the addition of TMS acetylide. Amano Enzyme Inc. is acknowledged with thanks for the gift of lipase PS-C. This work was supported both by a Grant-in-Aid for Scientific Research (no.18580106) and {\textquoteleft}High-Tech Research Center{\textquoteright} Project for Private Universities: matching fund subsidy 2006–2011 from the Ministry of Education, Culture, Sports, Science and Technology, Japan, and acknowledged with thanks. Copyright: Copyright 2009 Elsevier B.V., All rights reserved.",

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AU - Sugai, Takeshi

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N2 - While the first total synthesis of modiolide A (1a), a 10-membered ring lactone with a marine-origin was achieved, an important chiral building block for constructing the chirality at C-4 in 1a, (S)-6-[(4-methoxybenzyl)oxy]-1-trimethylsilyl-1-hexyn-3-ol (3a) was obtained in as high as 96.1% ee. Asymmetric reduction of a silylated propargyl ketone (5) mediated by whole-cell of Pichia minuta IAM 12215 was established. This yeast-mediated reduction was also applicable to provide stereochemically pure (3S,5R)-5-[(4-methoxybenzyl)oxy]-1-trimethylsilyl-1-hexyn-3-ol (15), a synthetic intermediate for the related 10-membered lactone, tuckolide (16).

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