Trifluoroacetic Acid-Mediated Cleavage of a Triethylsilyl Protecting Group: Application in the Final Step of the Semisynthetic Route to Paclitaxel (Taxol)
The final step of the semisynthetic route to paclitaxel involvescleavage of the triethylsilyl (TES) protecting group from theC-7 hydroxyl group. Paclitaxel is an extremely complex molecule, and standard deprotection conditions led to formationof several impurities. Trifluoroacetic acid in aqueous acetic acidwas found to be very effective in the cleavage of the TES groupwithout compromising the quality of the product.