Collect. Czech. Chem. Commun. 2011, 76, 1579-1594
https://doi.org/10.1135/cccc2011039
Published online 2011-12-23 10:44:00

Enantioselective synthesis of a taxol C ring

Cong Maa, Stéphanie Schiltza and Joëlle Prunetb,*

a Laboratoire de Synthèse Organique, CNRS UMR 7652, Ecole Polytechnique, DCSO, F91128 Palaiseau, France
b WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ, UK

Abstract

An enantioselective synthesis of a C ring of taxol has been accomplished. The key step is an oxidative cleavage of a derivative of the Wieland–Miescher ketone. A first attempt of a Shapiro reaction modelling the coupling of the C ring with the A fragment of taxol was also successful.

Keywords: Taxol; Wieland–Miescher ketone; Shapiro reaction; Synthesis design; Ozonolysis; Terpenoids.

References: 44 live references.

This article is part of virtual issue Prof. Pavel Kočovský, FRSE
60th Birthday.