Transition metal-catalysed A-ring C-H activations and C(sp²)-C(sp²) couplings in the 13α-oestrone series and in vitro evaluation of antiproliferative properties.

ABSTRACT: Facile syntheses of 3-O-carbamoyl, -sulfamoyl, or -pivaloyl derivatives of 13α-oestrone and its 17-deoxy counterpart have been carried out. Microwave-induced, Ni-catalysed Suzuki-Miyaura couplings of the newly synthesised phenol esters with phenylboronic acid afforded 3-deoxy-3-phenyl-13α-oestrone derivatives. The carbamate and pivalate esters proved to be suitable for regioselective arylations. 2-(4-Substituted) phenyl derivatives were synthesised via Pd-catalysed, microwave-assisted C-H activation reactions. An efficient, one-pot, tandem methodology was elaborated for the introduction of the carbamoyl or pivaloyl group followed by regioselective C-2-arylation and subsequent removal of the directing group. The antiproliferative properties of the novel 13α-oestrone derivatives were

SUBMITTER: Traj P 

PROVIDER: S-EPMC8008932 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature