Stereodivergent construction of cyclic ethers by a regioselective and enantiospecific rhodium-catalyzed allylic etherification: Total synthesis of gaur acid

被引：57

作者：

Evans, PA ^{[1
]}

Leahy, DK ^{[1
]}

Andrews, WJ ^{[1
]}

Uraguchi, D ^{[1
]}

机构：

[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 36期

关键词：

allylation; asymmetric synthesis; cyclic ethers; metathesis; rhodium;

D O I：

10.1002/anie.200460612

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A dramatic enhancement of the stereospecificity of the title reaction was observed with trimethylphosphite-modified copper(I) alkoxide reagents. The combination of this reaction with ring-closing metathesis provides a direct approach to cis- and trans-disubstituted cyclic ethers (see scheme). A seven-step total synthesis of the natural product gaur acid highlighted the potential of this methodology. LG = leaving group.

引用

页码：4788 / 4791

页数：4

共 35 条

[1]

Clark JS, 1997, TETRAHEDRON LETT, V38, P127

[2]

COREY EJ, 1979, TETRAHEDRON LETT, P399

[3] Asymmetric aldol-ring-closing metathesis strategy for the enantioselective construction of six- to nine-membered oxygen heterocycles [J].