A New Strategic Intermediate for β-Lactam Antibiotic Synthesis : Allenecarboxylates

概要

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Intra- and inter-molecular Michael addition of allenecarboxylates, derived from penicillins, may offer straightforward synthetic routes to 2-exo-methylenepenams and C (3) - substituted Δ3-cephems. Thus obtained 2-exo-methylenepenams are divergent intermediates for penem and penam families of antibiotics or potent β-lactamase inhibitors. The intermolecular Michael addition of the allenecarboxylates can achieve construction of the cephem framework as well as introduction of various C (3) -substituents, e.g., amino, sulfenyl, chloro, and alkenyl groups. In place of the allenecarboxylates, 3, 4-disubstituted 2- [4- (phenylsulfonylthio) -2-oxoazetidin- 1 -yl] -2-butenoates work as a promising precursor of both the 2-exo-methylenepenams and 3-chloro-Δ3-cephems.
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