6-deoxyanthracyclines

Details 6-deoxyanthracyclines 6-deoxyanthracyclines

C - Chemistry, Metallurgy

07

H

260/208.2

C07H 15/252 (2006.01) C07D 407/04 (2006.01)

Patent

CA 1234104

- Abstract of the Disclosure - A new process for the preparation of 6-deoxyanthracyclinones of general formula I; Image I wherein R represents a hydrogen atom, a hydroxy group or a lower alkoxy group is described. The process provides a total synthesis of the 6-deoxyanthracyclinones of formula I using a 1,2,3,6-tetrahydro-phthalate as starting material. The obtained racemic mixture of the compounds of formula I, if desired, can be submitted to optical resolution by the conventional method of conversion to diastereomeric deri- vatives using a chiral resolving agent. Alternatively, the racemic mixture can be used as such for the condensation with a suitably protected halosugar derivative to obtain alpha glycosidic derivatives of formula XV: Image XV wherein R1 represents a hydrogen atom or a hydroxy group, one of R2 and R3 represents a hydrogen atom, the other of R2 and R3 represents a hydrogen atom or a hydroxy group and X is a hydrogen atom or a trifluoro acetyl group. The N-trifluoroacetyl 7S:9S and 7R:9R deri vatives of the ?-glycosides of formula XV can be separa ted by chromatography on silica gel to obtain, after mild alkaline hydrolisis the wanted 7S:9S ?-glycosides (R1=H) as free hases and can eventually be transformed- into their corresponcling doxorubicin derivatives (R1=OH) by known procedures. These .alpha.-glycoside deriva- tives have anti-tumour properties.

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