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

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

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...

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Մատենագիտական մանրամասներ
Հիմնական հեղինակներ: Fekner, T, Baldwin, J, Adlington, R, Jones, T, Prout, C, Schofield, C
Ձևաչափ: Journal article
Լեզու:English
Հրապարակվել է: 2000
Նկարագրություն
Ամփոփում: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.

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