Tetrahedron

Synthesis of 3-functionalised cephalosporins by photoinitiated bromination: Transformations of 2, 2, 2-trichloroethyl 1S, 6R, 7R)-3-bromomethyl-7-formamidoceph-3- …

BR Cowley, DC Humber, B Laundon, AG Long…

Index: Cowley; Humber; Laundon; et al. Tetrahedron, 1983 , vol. 39, # 3 p. 461 - 467

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Citation Number: 11

Abstract

The 3-bromomethyl derivative 2c, obtained by photoinitiated bromination of the corresponding 3-Me compound 1c, has been converted into the antibiotics cephalothin 18 and cephaloridine 20. Reaction of 2c with lithium dimethyl-and diphenyl-cuprate led to the intermediates 22 and 24 respectively. Further transformation of 24 provided the 3-benzyl derivative 27, an isostere of cephaloridine.