Reactions of relevance to the chemistry of aminoglycoside antibiotics. Part 15. The selective modification of neamine by radical-induced deamination
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.