title: Diastereomeric fortimicin 1,2-epoxides. The preparation of the 1-deamino-2-deoxyfortimicins A and B and the 1,2-di-epi-fortimicins 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 beta-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.
mesh_terms: D000617:Aminoglycosides / Q000138:chemical synthesis / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D055598:Chemical Phenomena; D002621:Chemistry; D007536:Isomerism; D008968:Molecular Conformation; D009904:Optical Rotation
chemical_list: D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; C023385:fortimicin B; C023384:fortimicin A; C033971:1-deamino-2-deoxyfortimicin B; C033970:1-deamino-2-deoxyfortimicin A