A New Route to Semisynthetic Cephalosporins from Deacetylcephalosporin C. I. Synthesis of 3-Heterocyclicthiomethyl-cephalosporins

SUSUMU TSUSHIMA; MICHIYUKI SENDAI; MITSURU SHIRAISHI; MASAYASU KATO; NORICHIKA MATSUMOTO; KENZO NAITO; MITSUO NUMATA

doi:10.1248/cpb.27.696

SUSUMU TSUSHIMA, MICHIYUKI SENDAI, MITSURU SHIRAISHI, MASAYASU KATO, NORICHIKA MATSUMOTO, KENZO NAITO, MITSUO NUMATA

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Keywords: SCE-963

JOURNAL FREE ACCESS

1979 Volume 27 Issue 3 Pages 696-702

DOI https://doi.org/10.1248/cpb.27.696

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Abstract

New compounds 3-acetoacetoxymethyl-7β-acylaminoceph-3-em-4-carboxylic acids (4) were synthesized from deacetylcephalosporin C (3a), after N-protection of the amino-adipoyl group followed by acetoacetylation of the 3'-hydroxyl with diketene and acyl exchange at the 7-position. They underwent a facile nucleophilic displacement of the 3'-acetoacetoxy group with heterocyclic thiols to afford 7β-acylamino-3-heterocyclicthio-methylceph-3-em-4-carboxylic acids (6) including SCE-963 (6e) in good yields.

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