08 October 2009

New Paclitaxel Route?


The picture above comes from "C-H oxidation proves its worth" and describes a novel route to a macrolide; instead of using the usual esterification route, the authors used a catalytic coupling between a carboxylic acid and a methylene carbon.

Would this methodology be amenable to the synthesis of paclitaxel? If the usual 10-deactyl baccatin III were modified such that it lacked an OH at the appropriate position (C13): would it be possible to use the methodology outlined in the paper in order to synthesise the compound?

All of the above is academic, an appropriate protecting group choice for the side chain would be needed but ... if there was a natural source of 13-deoxy 10-deactyl baccatin III; the chemistry may be worth exploring.

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