N-Oxidation of Epothilone A-C and O-Acyl Rearrangement to C-19- and C-21-Substituted Epothilones

A bothersome side reaction in the last step of a total synthesis of epothilone led to the formation of the thiazol‐N‐oxide 1. Obtained from epothilones prepared by fermentation, these biologically active N‐oxides allow the extremely short synthesis of the highly active epothilones 2 with modified si...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 1999-07, Vol.38 (13-14), p.1971-1974
Main Authors: Höfle, Gerhard, Glaser, Nicole, Kiffe, Michael, Hecht, Hans-Jürgen, Sasse, Florenz, Reichenbach, Hans
Format: Article
Language:English
Subjects:
Antitumor agents
Macrocycles
Mycobacteria
Natural products
Structure-activity relationships
Online Access:Get full text
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Summary:A bothersome side reaction in the last step of a total synthesis of epothilone led to the formation of the thiazol‐N‐oxide 1. Obtained from epothilones prepared by fermentation, these biologically active N‐oxides allow the extremely short synthesis of the highly active epothilones 2 with modified side chains by an O‐acyl rearrangement.
ISSN:1433-7851
1521-3773
DOI:10.1002/(SICI)1521-3773(19990712)38:13/14<1971::AID-ANIE1971>3.0.CO;2-X