A bioinspired approach to tri-nor-guaianes.: Synthesis of (-)- clavukerin A

被引：13

作者：

Blay, Gonzalo ^{[1
]}

Garcia, Begona ^{[1
]}

Molina, Eva ^{[1
]}

Pedro, Jose R. ^{[1
]}

机构：

[1] Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Burjassot, Valencia, Spain

来源：

JOURNAL OF NATURAL PRODUCTS | 2006年 / 69卷 / 08期

关键词：

D O I：

10.1021/np060184g

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

A bioinspired approach to tri-norguaianes by degradation of the C-7 side chain of related guaia-11-enes is described. In this approach (-)-clavukerin A (1) is obtained by selective ozonolysis-Criegge rearrangement of (+)-1 alpha H, 7H, 10 alpha H-guaia-4,11-dien-3-one (4) to afford 7 beta-hydroxy and 7 beta-acetoxy tri-nor-guaiane derivatives 6 and 7, respectively, which after elimination and deoxygenation give the title compound. The starting guaiadienone is readly obtained from commercially available santonin or (+)-dihydrocarvone.

引用

页码：1234 / 1236

页数：3

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