Nature-Inspired Stereospecific Total Synthesis of P-(+)-Dispegatrine and Four Other Monomeric Sarpagine Indole Alkaloids

被引：45

作者：

Edwankar, Chitra R. ^{[1
]}

Edwankar, Rahul V. ^{[1
]}

Deschamps, Jeffrey R. ^{[2
]}

Cook, James M. ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem & Biochem, Milwaukee, WI 53201 USA

[2] USN, Res Lab, Ctr Biomol Sci & Engn, Washington, DC 20375 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 47期

关键词：

alkaloids; biaryls; C-C coupling; natural product synthesis; thallium; BIOLOGY-ORIENTED SYNTHESIS; BIARYL COUPLING REACTION; THALLIUM(III) TRIFLUOROACETATE; AROMATIC NUCLEI; PRODUCTS; DISCOVERY; BIOSYNTHESIS; MACROLINE; WELL;

D O I：

10.1002/anie.201206015

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

All five: The first total synthesis of the C2-symmetric indole alkaloid 1 involved a late-stage thallium(III) acetate-mediated intermolecular oxidative coupling to construct the C9-C9' bond with complete regio- and stereocontrol. The formation of a single atropodiastereomer in this critical step arises from internal asymmetric induction. The first total synthesis of four other monomeric sarpagine indole alkaloids is also described. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：11762 / 11765

页数：4

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