Concomitant C-ring expansion and D-ring formation in lanosterol biosynthesis from squalene without violation of Markovnikov's rule

被引：90

作者：

Hess, BA ^{[1
]}

机构：

[1] Vanderbilt Univ, Dept Chem, Nashville, TN 37235 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 35期

关键词：

D O I：

10.1021/ja026850r

中图分类号：

O6 [化学];

学科分类号：

0703 [化学];

摘要：

A mechanism is proposed for the formation of the C and D rings of lanosterol from squalene on the basis of density functional calculations of a model cyclopentylcarbinyl carbocation. The mechanism involves the ring expansion of the cyclopentylcarbinyl carbocation to the six-membered ring C in concert with the formation of the D ring. The mechanism does not involve a violation of Markovnikov's rule as the earlier proposed mechanism does for the formation of rings C and D. Copyright © 2002 American Chemical Society.

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页码：10286 / 10287

页数：2

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