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
收藏
页码：4445 / 4446
页数：2
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