酯 - 亚胺缩合反应：用于合成碳青霉烯抗生素PS - 5和PS - 6的外消旋中间体的制备

Ester-imine condensations: preparation of racemic intermediates for the synthesis of the carbapenem antibiotics PS-5 and PS-6.

作者信息

Ha D C, Hart D J

出版信息

J Antibiot (Tokyo). 1987 Mar;40(3):309-19. doi: 10.7164/antibiotics.40.309.

DOI:10.7164/antibiotics.40.309

Abstract

The lithium enolates of ethyl butyrate and ethyl isovalerate react with N-p-methoxyphenylcinnamaldimine in tetrahydrofuran (THF)-hexamethylphosphoric triamide (HMPA) to afford predominantly trans beta-lactams 9 (67%) and 20 (78%), respectively. beta-Lactam 9 was converted to PS-5 intermediate 18 in 21% overall yield (8 steps). Beta-lactam 20 was converted to PS-6 analog 28 in 22% overall yield using an eight step sequence.

摘要

丁酸乙酯和异戊酸乙酯的烯醇锂盐在四氢呋喃（THF）-六甲基磷酰胺（HMPA）中与N-对甲氧基苯基肉桂醛亚胺反应，分别主要生成反式β-内酰胺9（67%）和20（78%）。β-内酰胺9以21%的总收率（8步）转化为PS-5中间体18。使用八步反应序列，β-内酰胺20以22%的总收率转化为PS-6类似物28。