Process for preparing 4-demethoxydaunomycinone

Details Process for preparing 4-demethoxydaunomycinone Process for preparing 4-demethoxydaunomycinone

C - Chemistry, Metallurgy

07

C

260/208

C07C 50/38 (2006.01) C07C 46/00 (2006.01)

Patent

CA 1337762

(+) 4-Demethoxy-daunomycinone (I): Image (I) the known aglycone of 4-demethoxy-daunomrubicin, is prepared by protecting the 13-keto group of 4-demethyldaunomycinone, by means of ethylene glycol to from a 13-dioxolanyl derivative, sulfonylating the 4-hydroxy group, reacting the sulfonylated compound, in a appropriate reducing environment, with a catalytic amount of a transition metal complex, preferably palladium or nickel with 1,3 diphenylphosphinopropane or 1,1'- bis(diphenyl-phosphino) ferrocene, and eliminating the 13- dioxolanyl group by treatment with trifluoroacetic acid. In comparison with the processes described in the prior art, wherein a racemic mixture of the wanted product was obtained, the present process permits the retaining of optical purity throughout the synthesis, no use of dangerous chemical reagents, easiness and smoothness for achieving in few steps and good yields the desired results.

596190

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