Synthesis of 2'-deoxy-L-fucopyranosylcarminomycinone and -epsilon-pyrromycinone as well as 2'-deoxy-D-erythro-pentopyranosyldaunomycinone, -carminomycinone, and -epsilon-pyrromycinone.
Treatment of di-O-acetyl-2-deoxy-L-fucopyranosyl bromide with carminomycinone and epsilon-pyrromycinone in the presence of mercuric bromide and mercuric cyanide afforded 3',4'-diO-acetyl-2'-deoxy-L-fucopyranosylcarminomycinone and -epsilon-pyrromycinone. Similarly, when di-O-acetyl-2-deoxy-D-erythrho-pentopyranosyl chloride was treated with daunomycinone, carminomycinone and epsilon-pyrromycinone, the di-O-acetyl derivatives of the anthracyclinone glycosides were obtained. Deacetylation of the previous acetates with sodium methoxide afforded 2'-deoxy-L-fucopyranosylcarminomycinone and -epsilon-pyrromycinone, as well as 2'-deoxy-D-erythro-pentopyranosyldaunomycinone, -carminomycinone, and -epsilon-pyrromycinone. 2'-Deoxy-L-fucopyranosylcarminomycinone was found to be more active than carminomycin at higher dosages on L1210.
D000818:Animals; D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D001419:Bacteria / Q000187:drug effects; D002360:Carubicin / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D051379:Mice; D009279:Naphthacenes / Q000138:chemical synthesis* / Q000494:pharmacology
D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic; D009279:Naphthacenes; C009142:epsilon-pyrromycinone; C015736:carminomycinone; D002360:Carubicin