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Total Synthesis of the Monoterpenoid Indole Alkaloid (±)‐Aspidophylline A
Author(s) -
Teng Mingxing,
Zi Weiwei,
Ma Dawei
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201310928
Subject(s) - alkaloid , intramolecular force , chemistry , piperidine , indole alkaloid , natural product , total synthesis , stereochemistry , oxidative coupling of methane , structural motif , organic chemistry , biochemistry , catalysis
Aspidophylline A belongs to the akuammiline alkaloid family, the members of which possess intriguing cagelike structures and diverse biological activities. Herein we report a 15‐step synthesis of this alkaloid from conveniently available starting materials. The key elements of the synthesis include an intramolecular oxidative coupling to create the tetracyclic furoindoline motif of the natural product and a [Ni(cod) 2 ]‐mediated cyclization to install its piperidine ring.