Aminoglycoside antibiotics: Chemical conversion of neomycin B, paromomycin, and lividomycin B into bioactive pseudosaccharides

Abstract

Pseudosaccharides containing various natural combinations of rings present in aminoglycoside antibiotics were prepared from the parent antibiotics, neomycin B, paromomycin, and lividomycin B, by oxidation of available vicinal diols and β-elimination. Pseudotrisaccharides comprising rings A, B, and C of paromomycin and lividomycin B, a pseudotrisaccharide comprising rings B, C, and D of the three antibiotics, and a 'core' pseudotrisaccharide containing rings B and C were thus prepared. These are valuable biological probes and intermediates for semisynthetic work in this series.