Iterative direct aldol strategy for polypropionates: Enantioselective total synthesis of (-)-membrenone a and B

Kaliyamoorthy Alagiri; Shaoquan Lin; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1021/ol5024932

Iterative direct aldol strategy for polypropionates: Enantioselective total synthesis of (-)-membrenone a and B

Kaliyamoorthy Alagiri, Shaoquan Lin, Naoya Kumagai, Masakatsu Shibasaki

研究成果: Article › 査読

18 被引用数 (Scopus)

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An iterative direct aldol reaction using a C3 propionate unit as an aldol donor offers expeditious access to polyketide assembly in a highly diastereo- and enantioselective manner. An all-syn polyketide array with four consecutive stereogenic centers was efficiently constructed by an aldol reaction of thiopropionamide via soft Lewis acid/hard Brønsted base cooperative catalysis. This iterative aldol strategy led to an enantioselective synthesis of (-)-membrenone A and B. (Chemical Equation Presented).

本文言語	English
ページ（範囲）	5301-5303
ページ数	3
ジャーナル	Organic Letters
巻	16
号	20
DOI	https://doi.org/10.1021/ol5024932
出版ステータス	Published - 2014 10月 17
外部発表	はい

ASJC Scopus subject areas

生化学
物理化学および理論化学
有機化学

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10.1021/ol5024932

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AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

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AB - An iterative direct aldol reaction using a C3 propionate unit as an aldol donor offers expeditious access to polyketide assembly in a highly diastereo- and enantioselective manner. An all-syn polyketide array with four consecutive stereogenic centers was efficiently constructed by an aldol reaction of thiopropionamide via soft Lewis acid/hard Brønsted base cooperative catalysis. This iterative aldol strategy led to an enantioselective synthesis of (-)-membrenone A and B. (Chemical Equation Presented).

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Iterative direct aldol strategy for polypropionates: Enantioselective total synthesis of (-)-membrenone a and B

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