Download PDF
Synthesis 2000; 2000(6): 869-882
DOI: 10.1055/s-2000-6263
special topic
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Synthesis of BC Ring-Systems of Taxol by Ring-Closing Metathesis

Damien Bourgeois* , Jacqueline Mahuteau, Ange Pancrazi, Steven P. Nolan, Joëlle Prunet
  • *Laboratoire de Synthèse Organique, associé au CNRS, Ecole Polytechnique, DCSO, F-91128 Palaiseau, France; Fax +33 (1) 69 33 30 10; E-mail: Joelle.Prunet@polytechnique.fr
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Highly functionalized BC ring-systems of Taxol® having the required chemistry for the C1, C2 and C8 centers have been synthesized using a ring-closing metathesis (RCM) reaction as the key step. Silylene 26 and acetonide 27 were obtained in excellent yields with Schrock's and our recently reported catalyst. In the case of carbonate 23, a trans cyclooctene was formed when using Grubbs' catalyst, indicating that RCM does not always proceed to completion of thermodynamic equilibrium.

cyclooctenes - cyclization - metathesis - olefin - Taxol - ruthenium - molybdenum