Syntheses of (6S)-cephalosporins from 6-aminopenicillanic acid

Journal article

Two practical routes to (6S,7S)-cephalosporins from 6-aminopenicillanic acid (6-APA) are described. In the first, 6-APA was converted to (2S,4S,5S,6S)-penicillin sulfoxide 49, which underwent Morin ring expansion to a protected (6S,7S)-cephem 50. In the second, ester 15 was converted to (2S,4S,5S,6R)-penicillin sulfoxide 58, which was then transformed into (6S,7R)-cephem 59. Different methods for the epimerisation of the C-7 position of cephem 59 were examined. (C) 2000 Elsevier Science Ltd.

Authors: Fekner, T; Baldwin, J; Adlington, R; Jones, T; Prout, C

• Publication status: Published
• Journal: TETRAHEDRON
• Volume: 56
• Issue: 33
• Pages: 6053-6074
• Publication date: 2000-08-11
• DOI: 10.1016/S0040-4020(00)00486-5
• ISSN: 0040-4020
• Language: English
• Keywords: rearrangements; cephalosporins; epimerisation; penicillins