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

GA Sulikowski, E Turos, SJ Danishefsky…

Index: Sulikowski, Gary A.; Turos, Edward; Danishefsky, Samuel J.; Shulte, Gayle M. Journal of the American Chemical Society, 1991 , vol. 113, # 4 p. 1373 - 1377

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Citation Number: 5

Abstract

Abstract: It has been found that diacetylation of the phenolic hydroxyl groups at C-6 and CI 1 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- ...