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

Research output: Contribution to journal › Article › peer-review

17 Citations (Scopus)

Abstract

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).

Original language	English
Pages (from-to)	5301-5303
Number of pages	3
Journal	Organic Letters
Volume	16
Issue number	20
DOIs	https://doi.org/10.1021/ol5024932
Publication status	Published - 2014 Oct 17
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "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 Br{\o}nsted base cooperative catalysis. This iterative aldol strategy led to an enantioselective synthesis of (-)-membrenone A and B. (Chemical Equation Presented).",

author = "Kaliyamoorthy Alagiri and Shaoquan Lin and Naoya Kumagai and Masakatsu Shibasaki",

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AU - Alagiri, Kaliyamoorthy

AU - Lin, Shaoquan

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

PY - 2014/10/17

Y1 - 2014/10/17

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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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