Tetrahedron

γ-Lactam analogues of penicillanic and carbapenicillanic acids

JE Baldwin, MF Chan, G Gallacher, M Otsuka, P Monk…

Index: Baldwin; Chan; Gallacher; Otsuka Tetrahedron, 1984 , vol. 40, # 21 p. 4513 - 4525

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Citation Number: 40

Abstract

Synthesis and biological activity of γ-lactam analogues of penicillanic and carboapenicillanic acids, and the sodium periodate mediated rearrangement of pyrrolidine- 2, 3-diones are described. 1, 3-Dipolar addition of cyclic nitrone (6) and methyl acrylate afforded the bicyclic adducts (7a) and (7b). Reductive cleavage of the NO bond and subsequent cyclisation of a regioisomer (11a) gave the γ-lactams (12a) and (12b) in a ...