Concise Photochemical Synthesis of the Antimalarial Indole Alkaloid Decursivine

被引：58

作者：

Mascal, Mark ^{[1
]}

Modes, Kyle V. ^{[1
]}

Durmus, Asuman ^{[1
]}

机构：

[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 19期

关键词：

antimalarials; indoles; natural products; photochemistry; total synthesis; ARTEMISININ RESISTANCE; TRYPTOPHAN; PHOTOLYSIS; PEPTIDES; MALARIA; CATION;

D O I：

10.1002/anie.201006423

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A four-step synthesis of the extracyclic, antimalarial indole natural product decursivine is described starting from commercial piperonyl bromide and serotonin (see scheme). A photoinitiated reaction cascade involving indole radical cation formation, rearrangement, radical recombination, rearomatization, elimination, and diastereoselective auto-acid-catalyzed closure of the dihydrofuran ring combine in a single step to conclude this remarkably efficient synthesis. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：4445 / 4446

页数：2

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