Process for the preparation of 4-demethoxydaunomycinone, the...

Details Process for the preparation of 4-demethoxydaunomycinone, the... Process for the preparation of 4-demethoxydaunomycinone, the...

C - Chemistry, Metallurgy

07

C

167/182, 260/208

C07C 50/38 (2006.01) A61K 31/70 (2006.01) C07C 46/00 (2006.01) C07H 15/252 (2006.01)

Patent

CA 1339634

4-Demethoxy-daunomycinone I: (see fig.I) the known aglycone of 4-demethoxy-daunorubicin, is prepared by protecting the 13-keto group of 4-demethyl-daunomycinone, sulfonylating the 4-hydroxy group, reacting the sulfonylated compound with an amine, removing the amino protecting group from the resultant 4-demethyl-4-(protected amino)-13-dioxolanyl- daunomycinone, diazotising the thus-freed 4-amino group and reducing under mild conditions the resulting diazonium compound. This compound of formula I has utility as an intermediate in the formation of 4-demethoxydaunorubicin, a potent antitumor compound.

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