Iterative Direct Aldol Strategy for Polypropionates: Enantioselective Total Synthesis of (-)-Membrenone A and B

被引：18

作者：

Alagiri, Kaliyamoorthy ^{[1
]}

Lin, Shaoquan ^{[1
]}

Kumagai, Naoya ^{[1
]}

Shibasaki, Masakatsu ^{[1
,2
]}

机构：

[1] Inst Microbial Chem BIKAKEN, Shinagawa Ku, Tokyo 1410021, Japan

[2] ACT C, JST, Shinagawa Ku, Tokyo 1410021, Japan

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 20期

关键词：

CATALYTIC ASYMMETRIC ALDOL; THIOPYRAN ROUTE; STEREOSELECTIVE-SYNTHESIS; MEMBRENONE-C; S; N ACETALS; THIOAMIDES; DIASTEREOSELECTIVITY; (+)-MEMBRENONE-C; CONDENSATION; ATORVASTATIN;

D O I：

10.1021/ol5024932

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 Bronsted base cooperative catalysis. This iterative aldol strategy led to an enantioselective synthesis of (-)-membrenone A and B.

引用

页码：5301 / 5303

页数：3

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