A Concise, Biomimetic Total Synthesis of (+)-Davanone

被引：15

作者：

Morrison, Karen C. ^{[1
]}

Litz, Jonathan P. ^{[1
]}

Scherpelz, Kathryn P. ^{[1
]}

Dossa, Paul D. ^{[1
]}

Vosburg, David A. ^{[1
]}

机构：

[1] Harvey Mudd Coll, Dept Chem, Claremont, CA 91711 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 10期

基金：

美国国家科学基金会;

关键词：

ARTEMISIA-PALLENS; STEREOSELECTIVE-SYNTHESIS; BITE ANGLES; DAVANONE; SESQUITERPENE; BIOSYNTHESIS; ECONOMY;

D O I：

10.1021/ol900697w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise, biomimetic synthesis of the antifungal and antispasmodic natural product (+)-davanone is described. The key stereoselective reactions are a Sharpless asymmetric epoxidation, a thiazolium-catalyzed esterification, and a palladium-mediated cyclization. All carbons are derived from isoprene units and no protecting groups are used, permitting an atom- and redox-economical synthesis.

引用

页码：2217 / 2218

页数：2

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