An efficient and practical total synthesis of (+)-vincamine from L-aspartic acid

P Gmeiner, PL Feldman, MY Chu-Moyer…

Index: Gmeiner; Feldman; Chu-Moyer; Rapoport Journal of Organic Chemistry, 1990 , vol. 55, # 10 p. 3068 - 3074

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Citation Number: 104

Abstract

Synthesis of optically pure a-tert-butyl 0-methyl (2S, 3R)-3-ethylhexahydroquinolinate (18) in 54-59% yield from L-aspartic acid was the foundation for a practical synthesis of (+)- vincamine. Conversion of L-aspartic acid to 18 was accomplished via two routes. In the first route, esterification was followed by mono-N-alkylation to attach the three-carbon residue. Nitrogen protection and intramolecular C-alkylation gave the piperidine, which was ...