A concise synthesis of the functionalized [5-7-6] tricyclic skeleton of guanacastepene A

被引：21

作者：

Du, XH ^{[1
]}

Chu, HFV ^{[1
]}

Kwon, OY ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 48期

基金：

美国国家科学基金会;

关键词：

guanacastepene A; 5-7-6] tricycle; intermolecular Diels-Alder reaction; a tandem Michael addition/intramolecular Mukaiyama aldol reaction;

D O I：

10.1016/j.tetlet.2004.09.187

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The six membered ring of guanacastepene A was constructed by a Diels-Alder reaction of 1,1,4-trisubstituted diene to set up the correct relative stereochernistry at the C8 quaternary center and the remote C5 stereocenter. In 10 efficient steps from the Diels-Alder adduct 9, the desired highly functionalized [5-7-6] tricyclic skeleton 2 was synthesized. Key steps involve trimethylsilyl chloride (TMSCl) assisted Michael addition to form enol ether and the usage of the enol ether in the following intramolecular Mukaiyama aldol reaction to form the middle seven membered ring of guanacastepene A. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：8843 / 8846

页数：4

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