How Stable Are Epoxides? A Novel Synthesis of Epothilone B.
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.
Martin
HJ
Institut für Organische Chemie der Universität Wien Währinger Strasse 38, 1090 Wien (Austria).
Drescher
M
Mulzer
J