Page 163 - Phytochemistry 2 (06-PG 605)

Problems of taxol development as a drug:
Supply, Solubility, Relatively low potency, side effects
10-deacetyl baccatin III
Currently, all paclitaxel production uses plant cell
fermentation (PCF) technology.

Docetaxel is a semi-synthetic analogue of paclitaxol (Taxol)
docetaxcel (taxotere) differ from paclitaxel at two positions in
its structure.
-It has a hydroxyl functional group on carbon 10,
Where paclitaxel has an acetate ester
-a tert-butyl carbamate ester on C3- side chain
instead of the benzamide in paclitaxel.
The C10 functional group change causes docetaxel to
be more water soluble than paclitaxel.