Semisynthetic aminoglycoside antibacterials. Part IV. Synthesis of antibiotic JI-20A, gentamicin B, and related compounds

Abstract

The application of the Lemieux-Nagabhushan reaction to the synthesis of antibiotic JI-20A and gentamicin B from a suitably protected garamine derivative is described. 3′-Deoxy-6′-N-methyl analogues of antibiotic JI-20A and gentamicin B have also been prepared from garamine intermediates. The transformation of 3′-deoxygentamicin X₂ into the 6′-deoxy-6′-methylamino-derivative is discussed.