Highly stereocontrolled and efficient preparation of the protected, esterification-ready docetaxel (Taxotere) side chain

Article abstract of DOI:10.1021/jo00085a004

A high-yield synthesis of the p-methoxybenzylidene-protected docetaxel (Taxotere) side chain, a useful derivative for efficient, epimerization-free esterification of the 7,10-bis[(trichloroethoxy)carbonyl] derivative of 10-desacetylbaccatin III for the preparation of docetaxel, has been effected; the C-4 and C-5 stereocenters of the 1,3-oxazolidine are generated with complete (≥99%) stereocontrol whereas that at C-2 is produced with 96% selectivity.