Synthetic approaches to anthracycline antibiotic analogues in which the nitrogen atom of the carbohydrate portion is incorporated into a 1,2,3-triazolyl moiety were investigated. By using methyl 6-azido-2,6-dideoxy-B-D-- arabino -hexopyranoside and methyl 3-azido-2,3,6-tricieoxy--a-L- arabino -hexopyranoside, the corresponding glycosides (16~a,b - 1_8 a_,b) of carminomycinone and daunomycinone were • prepared. The desired heterocyclic system was developed directly with the C-3’ and C-6’ azido anthracyclines by means of a cycloaddition process to give 7-0-[6'-(4 1-(4,5--dicarboethoxy-1,2,3-triazolyl)-2', 6'-dideoxy-^-D- arabino --hexopyranosyll-carminomycinone (23) and -daunomycinone (22), and 3'-(4,5-dicarboethoxy-l,2,3-triazolyl)-4’-epi-daunomycin (24).
ASJC Scopus subject areas
- Organic Chemistry