Novel conversion reaction of β-lactam to γ-lactam. Synthesis of γ-lactam analogs of penam and penem antibiotics.

Abstract

Penam and penem derivatives having the acetic acid ester moiety at C-6 underwent the novel conversion to the γ-lactam analogs which would mimic a turn structure of the C-terminal dipeptide, d-alanyl- d-alanine, of the bacterial peptidoglycan. This reaction was applied to the synthesis of the γ-lactam analogs of penam and penem antibiotics.