Tandem enantioselective conjugate addition-cyclopropanation. Application to natural products synthesis

被引：46

作者：

Alexakis, A ^{[1
]}

March, S ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 25期

关键词：

D O I：

10.1021/jo026262w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A tandem asymmetric conjugate addition-cyclopropanation was developed, in which a cyclic or linear enone was converted to a TMS-protected 3-substituted-cyclopropanol in an efficient one-pot reaction. These compounds were then selectively cleaved to yield alpha-methyl-beta-alkyl ketones, alpha-methylene-enones, or chain extended gamma-alkyl-enones. This methodology was applied to the formal total synthesis of (-)-(S,S)-clavukerin A and (+)-(R,S)-isoclavukerin.

引用

页码：8753 / 8757

页数：5

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