SYNTHESIS AND BIOLOGICAL-ACTIVITY OF PARASUBSTITUTED 3'-PHENYL DOCETAXEL ANALOGS

An expedient route for semisynthetic para-modified 3'-phenyl docetaxel analogs is described using the initial regioselective iodination of t he oxazolidinecarboxylate 3. Palladium catalyzed coupling reactions of the iodo intermediate 4 with alkenyl and aryl boronic acids and alkyn es led after alkaline hydrolysis to a series of N,O-protected para-sub stituted phenylisoserines 6. Coupling with 10-deacetyl-7,10-O-diTroc-b accatin III followed by standard deprotections and acylation afforded the title analogs.