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Synlett 1995; 1995(SI): 529-532
DOI: 10.1055/s-1995-5264
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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
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Publication Date:
31 December 2000 (online)

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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.

Vincamine - asymmetric Michael addition - chiral imines - enaminolactams - Bischler-Napieralski cyclization