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Total Syntheses of (−)‐Huperzine Q and (+)‐Lycopladines B and C
Author(s) -
Hong Benke,
Li Houhua,
Wu Jinbao,
Zhang Jing,
Lei Xiaoguang
Publication year - 2015
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.201409503
Subject(s) - total synthesis , enamine , huperzine a , natural product , stereochemistry , chemistry , organic chemistry , catalysis , acetylcholinesterase , enzyme
Abstract Utilizing a late‐stage enamine bromofunctionalization strategy, the twelve‐step total synthesis of (−)‐huperzine Q was accomplished. Furthermore, the first total syntheses of (+)‐lycopladines B and C are described. An unprecedented X‐ray crystal structure of an unusual epoxyamine intermediate is also reported, and the synthetic application of this intermediate in natural product synthesis is demonstrated.