Paclitaxel → Taxane

Beteiligte Stoffe

Reaktionsschritte

In brief, the present invention relates to an improved semi-synthetic process to produce a taxane intermediate, which can ultimately be used to produce taxane derivatives, such as paclitaxel, docetaxel and canadensol and its derivatives. In the process of the present invention, the protected taxane intermediate from which the taxane derivative can be derived is produced in a yield of over 65% of a single isomer by direct esterification of a protected taxane of formula (I) with a single isomeric open chain phenyl isoserine side chain. By using a single isomeric phenyl isoserine side chain, a single isomeric taxane intermediate is obtained at a yield of over 65%. This is substantially greater than the 40% yield of the process advanced by Denis et al in U.S. Pat. No. 4,924,011. In addition, by using the same hydroxyl protecting group to protect both the C-7 position and the 2′-position on the phenylisoserine side chain, simplifies and reduces the reaction route. These are all features which would be recognised as being advantageous in industrial scale up of the present process.

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