Simple o-Quinodimethane Route to (+/-)-4-Demethoxydaunomycinone

Article abstract of DOI:10.1021/ja00398a020

The anthracycline antibiotics daunorubicin and adriamycin are important clinically useful drugs in the treatment of a number of human cancers.The structurally simplified synthetic analogues 4-demethoxydaunorubicin and 4-demethoxyadriamycin show much clinical promise.The synthesis of the corresponding aglycon (+/-)-4-demethoxydaunomycinone from the inexpensive dye intermediate quinizarin, utilizing o-quinodimethane intermediates, is discussed.