An enantioselective total synthesis of (+)- and (-)-saudin. Determination of the absolute configuration

被引：39

作者：

Boeckman, RK ^{[1
]}

Ferreira, MDR ^{[1
]}

Mitchell, LH ^{[1
]}

Shao, PC ^{[1
]}

机构：

[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 02期

关键词：

D O I：

10.1021/ja017194i

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A short efficient enantioselective synthesis of both (+)- and (-)-saudin, a naturally occurring hypoglycemic diterpene, is described. This synthesis establishes the absolute configuration of natural (-)-saudin for the first time. The key steps include the enantioselective construction of a dimethyl Hagemann's ester by an asymmetric Michael reaction and establishment of the key 1,3 disposed quaternary centers by means of a novel Ti(IV) promoted Claisen rearrangement. The assembly of the polycyclic ketal skeleton was likely under kinetic control proceeding via formation of the C1oxygen-C7 bond through an oxonium ion intermediate in the final stage. Copyright © 2002 American Chemical Society.

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页码：190 / 191

页数：2

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