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 journalArticle

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 languageEnglish
Pages (from-to)309-319
Number of pages11
JournalThe Journal of antibiotics
Volume40
Issue number3
DOIs
Publication statusPublished - 1987
Externally publishedYes

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

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