Reactions of relevance to the chemistry of aminoglycoside antibiotics. Part 15. The selective modification of neamine by radical-induced deamination
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 12,p. 2665-2669
- https://doi.org/10.1039/p19800002665
Abstract
The reaction of neamine tetraformamide tetra-acetate with phosphorous oxychloride and triethylamine has been studied. Isocyanide formation was found to proceed in stepwise fashion. The radical-induced reduction of the resultant derivatives by tri-n-butylstannane leads to the corresponding deaminatied aminoglycoside derivatives. In this way five new derivatives of neamine have been prepared for (eventual) biological evaluation.This publication has 2 references indexed in Scilit:
- Reduction of 6α-alkyl-6β-isocyanopenicillanates by tri-n-butyltin hydride. A stereoselective synthesis of 6β-alkylpenicillanatesJournal of the Chemical Society, Chemical Communications, 1979
- The role of the pseudo-disaccharide neamine as an intermediate in the biosynthesis of neomycinBiochemical Journal, 1976