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Synthesis and Conformational Analysis of ( E )‐9,10‐Dehydroepothilone B: A Suggestive Link between the Chemistry and Biology of Epothilones
Author(s) -
Yoshimura Fumihiko,
Rivkin Alexey,
Gabarda Ana E.,
Chou TingChao,
Dong Huajin,
Sukenick George,
Morel Florence F.,
Taylor Richard E.,
Danishefsky Samuel J.
Publication year - 2003
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.200351407
Subject(s) - epothilones , stereochemistry , epothilone , chemistry , double bond , organic chemistry
The most potent epothilone analogue reported to date was obtained by incorporation of an E double bond at C9C10 in the epothilone B series (see picture). Molecular modeling, NMR spectroscopic analysis, and chemical observations were used to rationalize the remarkable potency‐enhancing effect of the double bond.