Anionic ring expansion reactions of oxabicyclo[4.2.1]heptenones. An efficient entry into the carbon framework of oxygenated cembranoids

被引：18

作者：

Xu, Q ^{[1
]}

Weeresakare, M ^{[1
]}

Rainier, JD ^{[1
]}

机构：

[1] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA

来源：

TETRAHEDRON | 2001年 / 57卷 / 38期

基金：

美国国家科学基金会;

关键词：

oxygenated cembranoid; eleutherobin; ring expansion; fragmentation; heterocycles;

D O I：

10.1016/S0040-4020(01)00778-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxabicyclo[2.2.1]heptenones undergo 2-carbon ring expansion reactions when subjected to anionic condensations and Michael acceptors. They also undergo condensation, fragmentation, and elimination reactions in their anionic couplings with aldehydes. As an outgrowth of this interesting chemistry, we have been able to access the carbon skeleton of oxygenated cembranoids by subjecting bis-activated ene-yne 39 to the enolate from oxabicyclo[2.2.1]heptenone 1. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8029 / 8037

页数：9

共 30 条

[1] Synthesis of key intermediates for a concise and convergent approach to the marine natural product eleutherobin [J].