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Chiral Guanidine Catalyzed Annulation to the Core Structure of (‐)‐Huperzine A
Author(s) -
Pan QiangBiao,
Ma DaWei
Publication year - 2003
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20030210716
Subject(s) - chemistry , guanidine , annulation , huperzine a , catalysis , aldol reaction , bicyclic molecule , aldol condensation , stereochemistry , combinatorial chemistry , organic chemistry , enzyme , acetylcholinesterase
A bridged bicyclic compound (7), the key intermediate for the synthesis of (‐)‐huperzine A (1), was prepared by diastereoselective Michael‐aldol annulation of β‐keto ester (4) catalyzed by chiral guanidine (2). A variety of chiral catalysts, substrates and reaction conditions were tested.