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Enantioselective Synthesis of (+)‐Chamaecypanone C: A Novel Microtubule Inhibitor
Author(s) -
Dong Suwei,
Hamel Ernest,
Bai Ruoli,
Covell David G.,
Beutler John A.,
Porco John A.
Publication year - 2009
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.200805486
Subject(s) - colchicine , tubulin , enantioselective synthesis , microtubule , chemistry , cascade , stereochemistry , total synthesis , tandem , cascade reaction , combinatorial chemistry , catalysis , biochemistry , microbiology and biotechnology , biology , materials science , genetics , chromatography , composite material
A bicycle built for tubulin : The total synthesis of (+)‐chamaecypanone C has been achieved by using a tandem retro‐Diels–Alder/Diels–Alder cascade reaction (see scheme). Initial biological studies demonstrate that (+)‐chamaecypanone C is an inhibitor of tubulin assembly and binds at the colchicine site.