Glycosidic cleavage from anaerobic saponification of the heptaacetate of daunomycin hydroquinone

BA Schweitzer, TH Koch

Index: Schweitzer; Koch Journal of the American Chemical Society, 1993 , vol. 115, # 13 p. 5446 - 5452

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Abstract

Abstract: Saponification of the heptaacetate of daunomycin hydroquinone (6) with 7 equiv of lithium hydroxide to N-acetyldaunomycin hydroquinone (7) in argon-degassed tetrahydrofuran (THF)/water medium was reported earlier not to give rise to glycosidic cleavage to yield 7-deoxydaunomycinone (5)(J. Am. Chem. SOC. 1991, 113, 1373). The only product characterized after exposure to air was N-acetyldaunomycin (8). The result ...

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