Torsional steering controls the stereoselectivity of epoxidation in the guanacastepene a synthesis

被引：43

作者：

Cheong, PHY ^{[1
]}

Yun, H

Danishefsky, SJ

Houk, KN

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

[2] Columbia Univ, Dept Chem, New York, NY 10027 USA

[3] Sloan Kettering Inst Canc Res, Bioorgan Chem Lab, New York, NY 10021 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 08期

关键词：

D O I：

10.1021/ol052862g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselectivity of the key epoxidation step in the synthesis of guanacastepene A is shown to be controlled by torsional steering. In this particular epoxidation reaction, the transition structure energetic difference is enhanced by the great asynchronicity of the forming C-O bonds that intensifies the torsional interactions.

引用

页码：1513 / 1516

页数：4

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