A highly stereoselective divergent synthesis of bicyclic models of photoreactive sesquiterpene lactones

被引：30

作者：

Fuchs, Sebastien ^{[1
]}

Berl, Valerie ^{[1
]}

Lepoittevin, Jean-Pierre ^{[1
]}

机构：

[1] Univ Strasbourg, CNRS, Lab Dermatochim, Clin Dermatol,CHU, F-67091 Strasbourg, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 07期

关键词：

alpha-methylene-gamma-butyrolactones; asymmetric synthesis; palladium; allylic substitution; enantio selectivity; diastereoselectivity;

D O I：

10.1002/ejoc.200600611

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sesquiterpene lactones are natural stereochemically pure compounds, which show a number of biological activities. In order to study the reactivity of sesquiterpene lactones in biological systems, we describe herein the asymmetric synthesis of a simple model, the alpha-methylene-hexahydrobenzofuranone 1, which includes the alpha-methylene-gamma-butyrolactone moiety and presents all the different possible ring junctions. Enantioselectivity was obtained by asymmetric palladium-catalyzed allylic substitution, and diastereoselectivity was achieved by iodolactonization. This strategy afforded the different lactones with an enantiomeric excess of >98%. (C) Wiley-VCH Verlag GmbH & Co.

引用

页码：1145 / 1152

页数：8

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