Semisynthetic aminoglycoside antibacterials. Part 9. Synthesis of novel 1- and 3-substituted and 1- and 3-epi-substituted derivatives of sisomicin and gentamicin from the 1- and 3-oxo-derivatives

Abstract

The conversion of selectively protected gentamicin and sisomicin derivatives into the 1- and 3-oxo-compounds by reaction with 3,5-di-t-butyl-1,2-benzoquinone is described. By application of suitable reductive techniques these oxo-aminoglycosides have been converted into novel 1- and 3-epi-, 1- and 3-deamino-1- and -3-hydroxy-, 1- and 3-deamino-1- and -3-epi-hydroxy-, and 1-deamino-derivatives. A study of the ¹³C n.m.r. parameters of the 1-epi- and 1-deamino-derivatives has led to the assignment of novel solution conformations for these new aminoglycosides.