PURPOSE: To obtain the subject compound useful as an anti-cancer drug through three novel intermediates by protecting 13-keto group of natural 4-demethyl- daunomycin, and the compound is obtained through actualization, sulfonation, amination, removing a protective group, diazotization, and final reduction in sequence.
CONSTITUTION: Natural (+) daunomycin 1, a starting substance, is demethylated into 4-demetyl-daunomycin 2, which is acetalized into novel 4-demethyl-13- dioxolanyl-daunomycin 3, which is sulfonated to obtain a novel compound of formula 4 (R is alkyl, aryl), which is aminated to obtain a novel compound of formula 5 (R1, R2 are each H, phenyl), which is removed of its protective group into a compound of formula 6, which is diazotized into a compound of formula 7, which is reduced finally to obtain 4-demethoxy daunomycin of formula 8. The method is advantageous since natural (+) daunomycin is used as a starting substance and the number of processes is reduced.
BARUTERU KABURI
TEITSUTSUIAANO MARUTEINENGO
FURANKO FURANKARANCHI
| JPS532463A | 1978-01-11 |