New efficient and totally stereoselective copper allylic benzoyloxylation of sterol derivatives

被引：12

作者：

Brunel, JM ^{[1
]}

Billottet, L ^{[1
]}

Letourneux, Y ^{[1
]}

机构：

[1] Univ Paul Cezanne, Fac Sci & Tech St Jerome, INRA, Lab Synth & Etud Subst Nat Act Biol, F-13397 Marseille, France

来源：

TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 18期

关键词：

D O I：

10.1016/j.tetasy.2005.08.024

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new efficient and totally stereoselective copper allylic benzoyloxylation of sterol derivatives has been developed. This methodology has been successfully applied to the synthesis of 7 alpha-hydroxy DHEA and 7 alpha-hydroxy cholesterol in a two-step synthesis with high chemical yields (77% and 61% overall yield, respectively). A mechanistic rationale justifying the total stereoselectivity encountered has been proposed. (C) 2005 Elsevier Ltd. All rights reserved.

引用

页码：3036 / 3041

页数：6

共 38 条

[1] NEUROSTEROID METABOLISM - 7-ALPHA-HYDROXYLATION OF DEHYDROEPIANDROSTERONE AND PREGNENOLONE BY RAT-BRAIN MICROSOMES [J].