Journal of Organic Chemistry p. 405 - 406 (1983)
Update date:2022-09-26
Topics:
Penco, Sergio
Angelucci, Francesco
Arcamone, Federico
Ballabio, Marzia
Barchielli, Giovanna
et al.
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.
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