Regiospecific Total Synthesis of 6-Deoxyanthracyclines: 4-Demethoxy-6-deoxydaunorubicin

Article abstract of DOI:10.1021/jo00151a033

A regiospecific approach to 6-deoxyanthracyclinones, which has resulted in the synthesis of the novel anthracycline 4-demethoxy-6-deoxydaunorubicin, is reported.The construction of aglycone entails the coupling of the metalated 1,4-dimethoxynaphthalene with 2-carbomethoxy-4-acetylcyclohexanal.The new aldehyde was prepared from cis tetrahydrophthalic monoester via a regioselective acylation followed by conversion of the carboxylic group to a formyl group.The daunosaminyl glycoside showed on HeLa cells the same cytotoxicity as daunorubicin.