Tetrahedron

5-Isothiazolidinonyl and 5-isoxazolidinonyl radicals: Approaches to the biogenetic-type synthesis of β-lactams

JE Baldwin, ALJ Beckwith, AP Davis, G Procter…

Index: Baldwin; Beckwith; Davis; et al. Tetrahedron, 1981 , vol. 37, # 11 p. 2181 - 2189

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Citation Number: 12

Abstract

A possible mechanism for penicillin biosynthesis involves the rearrangement of a 5- isothiazolidinonyl radical (6) to a β-lactam. However, generation of the model radicals (13 and 20) did not lead to β-lactams. The analogous reaction of a 5-isoxazolidinonyl radical is the basis for a potential synthesis of clavulanic acid, but again the rearrangement was not observed in the model radical (24).