Synthesis of BC ring-systems of taxol by ring-closing metathesis

Abstract : 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.
Document type :
Journal articles
Complete list of metadatas

https://hal-polytechnique.archives-ouvertes.fr/hal-00954910
Contributor : Denis Roura <>
Submitted on : Tuesday, March 11, 2014 - 1:06:00 PM
Last modification on : Wednesday, July 31, 2019 - 9:38:02 AM

Identifiers

Citation

Damien Bourgeois, Jacqueline Mahuteau, Ange Pancrazi, Steven Nolan, Joëlle Prunet. Synthesis of BC ring-systems of taxol by ring-closing metathesis. SYNTHESIS, Georg Thieme Verlag, 2000, pp.869-882. ⟨10.1055/s-2000-6263⟩. ⟨hal-00954910⟩

Share

Metrics

Record views

151