Tetrahedron p. 2735 - 2740 (1980)
Update date:2022-09-26
Topics:
Shiozaki, Masao
Ishida, Noboru
Iino, Kimio
Hiraoka, Tetsuo
The cleavage and some modifications of the 7-amide group of cephamycins are described.Cephamycin derivatives 16b, c which were synthesized from the naturally occuring cephamycin C (16a) were converted to the corresponding oxamic acid derivatives 17a, e respectively by the reaction with oxalyl chloride and successive treatment with water.The reaction of the oxamic acid 17a with diphenylcarbodiimide gave 7-aminocephamycinoic acid (7-ACMA) benzhydryl ester (21a) which was further converted to cefoxitin (21c).These compounds 17a, b, c, d, e, f thus obtained from cephamycin C appear to be favorable intermediates for the syntheses of cephamycin analogues such as cefmetazole (28c).
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