ENANTIOSELECTIVE APPROACHES TO VINCA ALKALOIDS THROUGH THE ASYMMETRICMICHAEL REACTION USING CHIRAL IMINES

Authors
MEKOUAR K AMBROISE L DESMAELE D DANGELO J
Citation
K. Mekouar et al., ENANTIOSELECTIVE APPROACHES TO VINCA ALKALOIDS THROUGH THE ASYMMETRICMICHAEL REACTION USING CHIRAL IMINES, Synlett, (5), 1995, pp. 529-532
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
5
Year of publication
1995
Pages
529 - 532
Database
ISI
SICI code
0936-5214(1995):5<529:EATVAT>2.0.ZU;2-N
Abstract
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 thr ough a Bischler-Napieralski cyclization into indoloquinolizidines 26 a nd 30, precursors of the Vinca alkaloids.