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
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 8,p. 2168-2185
- https://doi.org/10.1039/p19810002168
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.This publication has 1 reference indexed in Scilit:
- Semisynthetic aminoglycoside antibacterials. Part V. Synthesis of pentosyl and related derivatives of garamineJournal of the Chemical Society, Perkin Transactions 1, 1976