Experimental study reports synthetic routes for novel beta-lactam cephem derivatives, highlighting pathways to modify cephalosporin antibiotics with electron-withdrawing groups.
New β‐lactam antibiotics. Cephem derivatives with electron withdrawing substituents at position 3 Oxidation of the 3‐formyl‐2‐cephem compound 1 according to Corey [6] gave 2‐cephem‐3‐carboxylic esters 4a, b, c (Scheme 1), which proved to be useful intermediates for the synthesis of cephalosporins bearing in position 3 a methoxycarbonyl group (10a, b, c, d / Scheme 2) or a carboxy group (20, 25, 30/Schemes 3, 4). The 3‐formyl‐3‐cephem compounds 31a, b could be transformed into cyano‐ (33a) or methoxyiminomethyl‐ (36a, c, d) cephems (Scheme 5), which represent further examples of cephalosporins with electron withdrawing groups in position 3.
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PETER et al. (1975) studied this question.
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