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- Title
Highly Efficient Formal [2+2+2] Strategy for the Rapid Construction of Polycyclic Spiroindolines: A Concise Synthesis of 11-Demethoxy-16- epi-myrtoidine.
- Authors
Zhu, Jun; Cheng, Yu ‐ Jing; Kuang, Xiao ‐ Kang; Wang, Lijia; Zheng, Zhong ‐ Bo; Tang, Yong
- Abstract
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.
- Subjects
POLYCYCLIC compounds; TRYPTAMINE; STEREOSELECTIVE reactions; STRYCHNOS; MALONATES
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 32, p9370
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201603991