Synthesis of the carbocyclic core of zoanthenol: Implementation of an unusual acid-catalyzed cyclization

被引:46
作者
Behenna, Douglas C. [1 ]
Stockdill, Jennifer L. [1 ]
Stoltz, Brian M. [1 ]
机构
[1] CALTECH, Div Chem & Chem Engn, Arnold & Mabel Beckman Labs Chem Synth, Pasadena, CA 91125 USA
关键词
alkaloids; asymmetric catalysis; cyclization; natural products;
D O I
10.1002/anie.200700430
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) A smokin' hot cyclization! When the racemic cyclization precursor is heated in neat trifluoroacetic acid, an unusual Friedel-Crafts-type cyclization forms the carbocyclic core of the marine alkaloid zoanthenol containing two all-carbon-substituted quaternary centers. Catalytic asymmetric alkylation allows entry into an enantioselective route. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4077 / 4080
页数:4
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