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Synlett 1995; 1995(SI): 529-532
DOI: 10.1055/s-1995-5264
DOI: 10.1055/s-1995-5264
letter
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Enantioselective Approaches to Vinca Alkaloids through the Asymmetric Michael Reaction using Chiral Imines
Further Information
Publication History
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