Paclitaxel synthesis from precursor compounds and methods of producing the same
AssigneeNaPro BioTherapeutics, Inc.
InventorsNicholas J. Sisti, Charles S. Swindell, Madhavi C. Chander
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Abstract
An efficient protocol for the synthesis of taxol, taxol analogs and their intermediates is described. The process includes the attachment of the taxol A-ring side chain to baccatin III and for the synthesis of taxol and taxol analogs with variable A-ring side chain structures. A rapid and highly efficient esterification of O-protected isoserine and 3-phenylisoserine acids having N-benzyoloxycarbonyl groups to the C-13 hydroxyl of 7-O-protected baccatin III is followed by a deprotection-acylation sequence to make taxol, celphalomanninne and various analogs, including photoaffinity labeling candidates.
Claims8
A process of producing paclitaxel from an intermediate compound having the general formula:
- ##STR30## wherein P.sub.1 is a hydrogenatable benzyl protecting group comprising the steps of deprotecting and acylating the intermediate compound at the nitrogen position of the A-ring side chain to replace the CBZ protecting group with PhCO, deprotecting the side chain at the C-2' position to replace P.sub.1 with H, and deprotecting at C-7 to replace the TES protecting group with H.
Dependencies are inferred from the claim text.