Effective enantioselective approach to α-aminoalkylacrylic acid derivatives via a synthetic equivalent of an asymmetric Baylis–Hillman reaction: application to the synthesis of two C-2′ hydroxymethyl analogues of docetaxel

Abstract

Two C-2′ hydroxymethyl analogues of docetaxel have been synthesized from 10-desacetyl baccatin III and enantiopure (3S)-3-(N-tert-butoxycarbonylamino)-2-methylene-3-phenylpropanoic acid; the latter was prepared via the use of a new method, which is discussed, as is the biological evaluation of the two new analogues.