Ester-Imine Condensations: Preparation of Racemic Intermediates for the Synthesis of the Carbapenem Antibiotics PS-5 and PS-6

Deok Chan Ha; David J. Hart

doi:10.7164/antibiotics.40.309

Ester-Imine Condensations: Preparation of Racemic Intermediates for the Synthesis of the Carbapenem Antibiotics PS-5 and PS-6

Deok Chan Ha, David J. Hart

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

The lithium enolates of ethyl butyrate (7) and ethyl isovalerate (19) react with N-p-methoxyphenylcinnamaldimine (8) in tetrahydrofuran (THF) - hexamethylphosphoric triamide (HMPA) to afford predominantly trans β-lactams 9 (67 %) and 20 (78 %), respectively. β-Lactam 9 was converted to PS-5 (5) intermediate 18 in 21 % overall yield (8 steps). β-Lactam 20 was converted to PS-6 (6) analog 28 in 22 % overall yield using an eight step sequence.

Original language	English
Pages (from-to)	309-319
Number of pages	11
Journal	The Journal of antibiotics
Volume	40
Issue number	3
DOIs	https://doi.org/10.7164/antibiotics.40.309
Publication status	Published - 1987
Externally published	Yes

ASJC Scopus subject areas

Pharmacology
Drug Discovery

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