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Enantioselective Total Synthesis of (+)‐Alstilobanine C, (+)‐Undulifoline, and (−)‐Alpneumine H
Author(s) -
Li Guang,
Gaeng Nicolas,
Piemontesi Cyril,
Wang Qian,
Zhu Jieping
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202103580
Subject(s) - enantioselective synthesis , oxonium ion , chemistry , total synthesis , stereochemistry , indole test , ring (chemistry) , cyclohexanone , ether , piperidine , organic chemistry , catalysis , ion
We report herein the enantioselective total synthesis of three monoterpene indole alkaloids, namely, (+)‐alstilobanine C, (+)‐undulifoline, and (−)‐alpneumine H. The key features of our synthesis include: a) introduction of chirality via enantioselective deprotonation of a prochiral 4‐substituted cyclohexanone; b) use of methoxymethyl (MOM) ether as both a hydroxyl protective group and a latent oxonium species for the formation of bridged oxepane and c) domino double reductive cyclization to build both the indole and the piperidine ring at the end of the synthesis. The synthesis confirmed the absolute configuration of these natural products assigned based on the biogenetic hypothesis.