Synlett 1995; 1995(SI): 529-532
DOI: 10.1055/s-1995-5264
letter
© 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.

Enantioselective Approaches to Vinca Alkaloids through the Asymmetric Michael Reaction using Chiral Imines

Khalid Mekouar, Lydia Ambroise, Didier Desmaële, Jean d’ Angelo*
  • *Unité de Chimie Organique Associée au CNRS, Centre d’Etudes Pharmaceutiques, Université Paris-Sud, 5 rue J.-B. Clément, 92296 Châtenay-Malabry, France
Further Information

Publication History

Publication Date:
31 December 2000 (online)

Two enantioselective approaches to Vinca alkaloids were reported. Both used chiral enamine 15 which was exposed to methyl acrylate or methyl 2-acetoxyacrylate, leading to adducts 16 and 27 respectively, with an excellent stereoselectivity. These compounds were then converted through a Bischler-Napieralski cyclization into indoloquinolizidines 26 and 30, precursors of the Vinca alkaloids.