Process for converting 9-dihydro-13-acetylbaccatin iii into docetaxel or paclitaxel

Abstract

Processes for the preparation of docetaxel and paclitaxel or analogs from 9-dihydro-13-acetylbaccatin III via key intermediates (4), (5), (6), (6'), (8) and (8') or via intermediate (12) as well as processes for the preparation of said intermediates are disclosed. Said processes involve, in particular, oxidation of the hydroxy group at C-10, reaction with side chain precursors and intramolecular isomerisation of the oxo at C-10 to produce the 9-oxo isomer. Paclitaxel and docetaxel are useful in the treatment of cancer. Formulae (I), (II), (III).

Description

field of invention The invention relates to a method for preparing anticancer drug docetaxel or paclitaxel. More specifically, the present invention relates to a method for the synthesis of docetaxel or paclitaxel from 9-dihydro-13-acetylbaccatin III, wherein 9-dihydro-13-acetylbaccatin III is isolated from Taxane compounds of the Canadian yew (Taxus canadensis), an evergreen shrub that grows in eastern Canada and the northeastern United States. Background technique Taxanes are substances that occur naturally in yew trees such as the Canadian yew common in eastern Canada and the northeastern United States. 9-dihydro-13-acetylbaccatin III is one of the chemicals extracted from the needles of Taxus chinensis, and is used especially to produce 10-deacetylbaccatin III, which is used for the preparation of paclitaxel and its analogs useful intermediates. The taxane family of terpenes is considered an extremely promising group of cancer chemotherapeutic agents. Many taxane de...

AI Technical Summary

Problems solved by technology

However, the supply of 10-deacetylbaccatin III is limited to date due to limited biomass resources and low isolation yields (50-165 mg / kg taxus baccata needles). To

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