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Studies on β-lactam antibiotics. I. A novel conversion of penicillins into cephalosporins

✍ Scribed by Takashi Kamiya; Tsutomu Teraji; Yoshihisa Saito; Masashi Hashimoto; Osamu Nakaguchi; Teruo Oku

Publisher: Elsevier Science
Year: 1973
Tongue: French
Weight: 217 KB
Volume: 14
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)96303-8

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✦ Synopsis

The sulfenic acid intermediate (A) formed by a thermal sigmatropic rearrangement of penicillin sulfoxides (I) has been trapped either intramolecularly or intermolecularly by several methods. 1) Our efforts have been directed to the preparation of a key intermediate useful for syntheses of modified B-lactam antibiotics. We found that dithioazetldinones (II), 2) easily obtained from reactions of penicillin sulfoxides (I) with heteroaromatic thiols, are the key intermediates for preparing 2-halomethyl-penams (III) and cephams (IV) derivatives. This paper reports a novel conversion of penicillins into cephalosporins through these important key intermediates.

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