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How Stable Are Epoxides? A Novel Synthesis of Epothilone B
Author(s) -
Martin Harry J.,
Drescher Martina,
Mulzer Johann
Publication year - 2000
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/(sici)1521-3773(20000204)39:3<581::aid-anie581>3.0.co;2-w
Subject(s) - epoxide , dihydroxylation , olefin fiber , chemistry , stereochemistry , combinatorial chemistry , epothilone , enantioselective synthesis , organic chemistry , catalysis
Remarkable stability of the oxirane function is displayed over a number of synthetic operations in a novel synthesis of the antitumor compound epothilone B (see scheme). The cis ‐epoxide, generated very early by dihydroxylation of an ( E )‐olefin, was resistant to more than ten synthetic steps under a wide variety of reaction conditions. TBS= tert ‐butyldimethylsilyl.