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Asymmetric Synthesis of Bioactive Hydrodibenzofuran Alkaloids: (−)‐Lycoramine, (−)‐Galanthamine, and (+)‐Lunarine
Author(s) -
Chen Peng,
Bao Xu,
Zhang LeFen,
Ding Ming,
Han XiaoJie,
Li Jing,
Zhang GuoBiao,
Tu YongQiang,
Fan ChunAn
Publication year - 2011
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.201103198
Subject(s) - stereocenter , enantioselective synthesis , stereochemistry , quaternary carbon , michael reaction , chemistry , combinatorial chemistry , organic chemistry , catalysis
Divergent route : A direct CC bond‐forming approach to the key aryl‐substituted all‐carbon quaternary stereogenic center present in bioactive hydrodibenzofuran alkaloids has been discovered. This approach involves an unprecedented organocatalytic enantioselective Michael addition of α‐cyanoketones with acrylates (see scheme) and was used in a novel and divergent synthetic strategy for the title compounds in asymmetric fashion.