32385-10-7Relevant academic research and scientific papers
An entry to the ring B:Ring C bishydroquinone leucodaunomycin series containing an intact carbohydrate
Sulikowski, Gary A.,Turos, Edward,Danishefsky, Samuel J.,Shulte, Gayle M.
, p. 1373 - 1377 (2007/10/02)
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.
