Eric Didier

2-Monosubstituted-1,3-oxazolidines as improved protective groups of N-boc-phenylisoserine in docetaxel preparation

Abstract A new route for semisynthetic docetaxel, 1, is described using 2-monosubstituted-4-phenyl-1,3-oxazolidine-5-carboxylic acids in esterification of 7,10-O-diTroc-10-desacetylbaccatin III (4). Subsequent deprotection of esters 10(+10′) afforded title compound 1 without removal of the Boc group.

Expeditious semisynthesis of docetaxel using 2-trichloromethyl-1,3-oxazolidine as side-chain protection

Chloral reacts with phenylisoserine and N-Boc-phenylisoserine methyl esters to give N-unprotected 2-trichloromethyl-1,3-oxazolidines 4+4′. The corresponding oxazolidinecarboxylic acids 5+5′ were esterified by 10-desacetyl-7,10-diTroc-baccatin III. Concomitant deprotection of the Troc and 2-trichloromethylmethylene groups was achieved under reducing conditions (Zn, AcOH). The recovered product 7 was acylated with di-tert-butyldicarbonate to give docetaxel 1.

Methyleniminium salts as acylating agent — one step synthesis of baccatin III from 10-deacetylbaccatin III with high selectivity

Abstract New methyleniminium salts were investigated as acylating agent of 10-deacetylbaccatin III. Thus, synthesis of baccatin III was performed in one step with 79% isolated yield and 98% selectivity using the iminium salt prepared from mesyl chloride and N-ethylacetamide.