1978•HeterocyclesOpen access

Synthetic Studies on b-Lactam Antibiotics 9. Trans-formations of Penicillin to 3'-Substituted Cephalosporins

Shoichiro Uyeo, Tsutomu Aoki, H. ITANI, Teruji Tsuji, Wataru Nagata

Abstract

An important antibiotic cephalothin fi was prepared from 28-acetoxymethyl penicillin asulfoxide s which was derived from penicillin.Chemical conversion of penicillins into 3'-functionalized cephalosporins has been a subject of intensive studies.' We now wish to report our own work in this field.In a previous paper of this series,2 we reported a useful method for preparing 28-functionalized-methyl penicillin asulfox'.des.The present paper deals with conversion of one of these a-sulfoxides -la into cephalosporanate +.Although every attempt to convert directly into & by the Morin rearrangement under various experimental conditions failed,3 we could accomplish preparation of the cephem & by

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Key concepts: Penicillin, Cephem, Cephalosporin, Chemistry, Antibiotics, Lactam, Cephalosporin Antibiotic, Combinatorial chemistry