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
收藏
页码：2217 / 2218
页数：2
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