Process for the preparation of 7-hydroxy taxanes

Details Process for the preparation of 7-hydroxy taxanes Process for the preparation of 7-hydroxy taxanes

C - Chemistry, Metallurgy

07

D

C07D 305/14 (2006.01) C07D 407/12 (2006.01) C07D 409/12 (2006.01) C07D 413/12 (2006.01) C07D 417/12 (2006.01)

Patent

CA 2186917

Process for the preparation of 7-hydroxy taxanes of general formula (I) from 7-trialkylsilyl taxanes of general formula (II), wherein R1 is hydrogen, alkoxy, acyloxy or alkoxyacetoxy, and Z is a hydrogen atom or a radical of general formula (III), wherein R2 is an optionally substituted benzyl radical or an R'2-O-CO- radical wherein R'2 is an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, bicycloalkyl, optionally substituted phenyl or heterocyclyl radical, R3 is an aromatic alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, naphthyl or heterocyclyl radical and either R4 is a hydrogen atom and R5 is a hydroxy function protecting group, or R4 and R5 together form a saturated 5- or 6-membered heterocyclic ring. In general formula (II), each R, which are the same or different, is an alkyl radical optionally substituted by a phenyl radical.

Process for the preparation of 7-hydroxy taxanes of general formula (I) from 7-trialkylsilyl taxanes of general formula (II), wherein R1 is hydrogen, alkoxy, acyloxy or alkoxyacotoxy, and Z is a hydrogen atom or a radical of general formula (III), wherein R2 is an optionally substituted benzyl radical or an R'2-O-CO- radical wherein R'2 is an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl bicycloalkyl, optionally substituted phenyl or heterocyclyl radical R3 is an aromatic alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, naphthyl or heterocyclyl radical and either R4 is a hydrogen atom and R5 is a hydroxy function protecting group, or R4 and R5 together form a saturated 5- or 6-membered heterocyclic ring. In general formula (II), each R, which are the same or different, is an alkyl radical optionally substituted by a phenyl radical.

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