An entry to the ring B:Ring C bishydroquinone leucodaunomycin series containing an intact carbohydrate

Article abstract of DOI:10.1021/ja00004a045

It has been found that diacetylation of the phenolic hydroxyl groups at C-6 and C-11 of daunomycin provides a product (see compound 12) that undergoes reduction of the ring C quinone to a hydroquinone without loss of the glycosyloxy function at C-7. Access to a stable heptaacetate (see compound 14) incorporating the nuclear bishydroquinone ensemble is thus provided. Basic hydrolysis of 14 accompanied by oxidation restores N-acetyldaunomycin. The success of this reaction reveals a surprising resistance to quinone methide formation via such leuco intermediates.