Portal de Periódicos da CAPES

Preparations of 2-epi-fortimicins A from 2-epi-fortimicin B by intramolecular base-catalyzed 2-O-acylation of 1,2′,6′-tri-N-benzyloxycarbonyl-2-epi-fortimicin B

1981; Elsevier BV; Volume: 92; Issue: 2 Linguagem: Inglês

10.1016/s0008-6215(00)80393-6

1873-426X

Jack Tadanier, Robert Hallas, Jerry R. Martin, MOMIR CIROVIC, RUTH S. STANASZEK,

Synthetic Organic Chemistry Methods

Preparations of 2-epi-fortimicin A (4) from 2-epi-fortimicin B (3) are described. In contrast to the previously reported, selective 4-N-acylation of 1,2′,6′-tri-N-benzyloxycarbonylfortimicin B (8) with N-(N-benzyloxycarbonylglycyloxy)succinimide, 1,2′,6′-tri-N-benzyloxycarbonyl-2-epi-fortimicin B (5) underwent predominant 2-O,4-N-diacylation under similar conditions. Proof of the structure of the diacylated product is presented, with evidence that the diacylated product is formed by initial intramolecular, base-catalyzed 2-O-acylation. The in vitro antibacterial activities of 2-epi-fortimicin A (4), 2-O-glycyl-2-epi-fortimicin A (11), 1-N-glycyl-2-epi-fortimicin A (12), and 5-deoxy-2-epi-fortimicin A (13) are reported.