Synthesis of 2/-Deoxy-L-fucopyranosylcarminomycinone and -e-pyrromycinone As Well As 2'-Deoxy-D-erythro-pentopyranosyldaunomycinone, -carminomycinone, and-e-pyrromycinone

Document Type

Article

Publication Date

1-1-1981

Abstract

Treatment of di-O-acetyl-2-deoxy-L-fucopyranosyl bromide with carminomycinone and e-pyrromycinone in the presence of mercuric bromide and mercuric cyanide afforded 3’,4'-di-0-acetyl-2,-deoxy-L-fucopyranosylcarminomycinone and -e-pyrromycinone. Similarly, when di-O-acetyl-2-deoxy-D-erytrho-pentopyranosyl chloride was treated with daunomycinone, carminomycinone and e-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 -e-pyrromycinone, as well as 2'-deoxy-D-eryhro-pentopyranosyldaunomycinone, -carminomycinone, and -e-pyrromycinone. 2'-Deoxy-L-fucopyranosylcarminomycinone was found to be more active than carminomycin at higher dosages on L1210. © 1981, American Chemical Society. All rights reserved.

Publication Title

Journal of Medicinal Chemistry

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