Organic letters

Stereoselective synthesis of 12, 13-cyclopropyl-epothilone B and side-chain-modified variants

R Schiess, J Gertsch, WB Schweizer, KH Altmann

Index: Schiess, Raphael; Gertsch, Juerg; Schweizer, W. Bernd; Altmann, Karl-Heinz Organic Letters, 2011 , vol. 13, # 6 p. 1436 - 1439

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Citation Number: 17

Abstract

A general strategy has been devised for the stereoselective synthesis of 12, 13-cyclopropyl- epothilone B and side-chain-modified variants thereof, which relies on late stage introduction of the heterocycle through Wittig olefination of ketone 14. Formation of the macrocycle was achieved through RCM-based ring closure and introduction of the cyclopropane moiety involved a highly selective Charette cyclopropanation of allylic ...