Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 32, Pages 9224-9228Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201603991
Keywords
diastereoselectivity; indole alkaloids; polycyclic indolines; tandem reactions; tryptamine derivatives
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Funding
- National Natural Sciences Foundation of China [21421091, 21432011, 21272250]
- National Basic Research Program of China (973 Program) [2015CB856600]
- Chinese Academy of Sciences
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A novel formal [2+2+2] strategy for the stereoselective elaboration of polycyclic indole alkaloids is described. Upon treatment with the catalyst InCl3 (5 mol%), tryptamine-derived enamides reacted readily with methylene malonate, thus enabling rapid and gram-scale access to versatile tetracyclic spiroindolines with excellent diastereoselectivity (21 examples, up to 95% yield, up to d.r.> 95: 5). This strategy provides a concise approach to alkaloids isolated from Strychnos myrtoides, as demonstrated by a short synthesis of 11-demethoxy-16-epi-myrtoidine.
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