2-epi-fortimicin B. Participation of 1-N-benzyloxycarbonylamino and 1-acetamido groups in solvolysis of 2-O-(methylsulfonyl)fortimicin B derivatives

Synthesis of 2-epi-fortimicin B has been accomplished by processes involving solvolyses of both 1-N-benzyloxycarbonyl- and 1-N-acetyl-2-O-(methylsulfonyl)fortimicins B, which occur with participation of the carbonyl oxygen atoms of the 1-N-acyl groups. The results illustrate both the greater effectiveness of acetamido groups in neighboring-group participation relative to benzyloxycarbonylamino groups, and the sensitivity of the nature of the products to the reaction conditions.