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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 22期

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

页码：4077 / 4080

页数：4

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