DIASTEREOMERIC FORTIMICIN 1, 2-EPOXIDES THE PREPARATION OF THE 1-DEAMINO-2-DEOXYFORTIMICINS A AND B

Abstract

The preparation of 1, 2-anhydro-2', 6'-di-N-benzyloxycarbonyl-1 -deaminofortimicin B-4, 5-carbamate (4) and its conversion to the two diastereomeric 2', 6'-di-N-benzyloxycarbonyl-1-deamino-2-deoxy-1, 2-epoxyfortimicin B-4, 5-carbamates 7 and 13 are described. The olefin 4 was used for preparation of 1-deamino-2-deoxyfortimicin A (6d) while the β-epoxide 13 was used for the preparation of 1, 2-di-epi-fortimicin A (17b) and 2-amino-1-deamino-2-deoxy-1-hydroxyfortimicin A (19c). The in vitro antibacterial activities of 6d, 17b and 19c are reported.