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

P Gmeiner, PL Feldman, MY Chu-Moyer…

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

全文：HTML全文

被引用次数: 105

摘要

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 ...