Conversion of 9-dihydro-13-acetylbaccatin iii to baccatin...

Details Conversion of 9-dihydro-13-acetylbaccatin iii to baccatin... Conversion of 9-dihydro-13-acetylbaccatin iii to baccatin...

C - Chemistry, Metallurgy

07

D

C07D 305/14 (2006.01)

Patent

CA 2403429

Novel methods and synthetic intermediates to prepare baccatin III and 10- deacetylbaccatin from readily available 9-dihydro-13-acetylbaccatin III are described. Selective protection and deprotection of the C-7 hydroxyl functionality provides an entry into facile synthesis of novel taxol intermediates, as well as, providing new methods for the preparation of paclitaxel and docetaxel in large scale. Selective oxidation of the C-9 hydroxyl without the need for protection of the C-7 hydroxyl is described.

L'invention concerne des nouveaux procédés et des nouveaux intermédiaires de synthèse, servant à préparer la baccatine III et la 10-désacétylbaccatine, à partir d'une 9-dihydro-13-acétylbaccatine III facilement disponible. La protection et déprotection sélectives de la fonctionnalité hydroxyle en C-7 permettent une exécution facile de la synthèse de nouveaux intermédiaires taxol, de même qu'elles permettent l'exécution de nouveaux procédés de préparation, à grande échelle, de paclitaxel et docétaxel. L'invention concerne également l'oxydation sélective de l'hydroxyle en C-9, sans qu'il soit nécessaire de protéger l'hydroxyle en C-7.

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