The semi-synthesis of a protected bacatin iii compound

C - Chemistry – Metallurgy – 07 – D

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C07D 305/14 (2006.01) C07F 7/10 (2006.01) C07F 7/18 (2006.01)

Patent

CA 2188190

The present invention relates to a semi-synthetic process to convert a naturally occurring taxane into a suitable starting material for the synthesis of paclitaxel (Taxol R) and related compounds. Specifically, the present invention relates to a process for the conversion of 9-dihydro-13-acetylbaccatin III into a 7-protected baccatin III which can then be used as starting material for the synthesis of taxane derivatives such as paclitaxel, docetaxel, cephalomannine and other taxanes structurally related to baccatin III. The method as described uses a preparative scale technique which is amenable to commercial scale-up.

L'invention porte sur un procédé semi-synthétique pour convertir un taxane naturel en une matière de départ pour la synthèse de paclitaxel (Taxol R) et de composés apparentés. Plus précisément, l'invention porte sur un procédé pour la conversion de la 9-dihydro-13-acétylbaccatine III en une baccatine III protégée en 7, qui peut servir comme matière de départ pour la synthèse de dérivés du taxane, p. ex. paclitaxel, docétaxel, céphalomannine et d'autres taxanes apparentés structurellement à la baccatine III. La méthode telle que décrite utilise une technique d'échelle préparatoire pouvant être adaptée à la mise à l'échelle commerciale.

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