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Asymmetric Total Syntheses of the Akuammiline Alkaloids (−)‐Strictamine and (−)‐Rhazinoline
Author(s) -
Li Wenfei,
Chen Zhitao,
Yu Di,
Peng Xin,
Wen Guohua,
Wang Siqi,
Xue Fei,
Liu XiaoYu,
Qin Yong
Publication year - 2019
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.201901074
Subject(s) - enantioselective synthesis , chemistry , total synthesis , intramolecular force , alkylation , intermolecular force , palladium , stereochemistry , molecule , combinatorial chemistry , organic chemistry , catalysis
Strictamine and rhazinoline are representative methanoquinolizidine‐containing akuammiline alkaloids that possess different stereochemistry at the C16 position. A unified approach to the enantioselective total syntheses of these two molecules is described. The key steps in this synthesis include a photocatalytic intra/intermolecular type II radical cascade reaction, a Tsuji–Trost allylation, a palladium‐ or nickel‐mediated cyclization, and a late‐stage intramolecular N‐alkylation reaction.
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