Syntheses of paclitaxel, analogs and intermediates with...

Details Syntheses of paclitaxel, analogs and intermediates with... Syntheses of paclitaxel, analogs and intermediates with...

C - Chemistry, Metallurgy

07

D

C07D 305/14 (2006.01) C07C 271/22 (2006.01) C07F 7/10 (2006.01)

Patent

CA 2155304

An efficient protocol for the synthesis of paclitaxel, paclitaxel analogs and their intermediates is described. The process includes the attachment of the paclitaxel A-ring side chain to baccatin III and for the synthesis of paclitaxel and paclitaxel analogs with variable A-ring side chain structures. A rapid and highly efficient esterification of O-protected isoserine and 3-phenylisoserine acids having N-benzyloxycarbonyl groups to the C-13 hydroxyl of 7-O-protected baccatin III is followed by a deprotection-acylation sequence to make paclitaxel, cephalomannine and various analogs, including photoaffinity labeling candidates. The chemical process of the present invention for the production of paclitaxel, paclitaxel analogs and their intermediates may be generalized, then, as the condensation of a compound of the general formula: (see formula I) with a taxane of the general structure: (see formula II) to give an intermediate of the general structure: (see formula III)

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