Synthesis of 2'-deoxy-L-fucopyranosylcarminomycinone and -epsilon-pyrromycinone as well as 2'-deoxy-D-erythro-pentopyranosyldaunomycinone, -carminomycinone, and -epsilon-pyrromycinone

Abstract

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.