Synthesis of novel steroid analogues containing nitrile and disulfide moieties via palladium-catalyzed cross-coupling reactions

Grundmannʹs ketone (3) was used as a common building block for introduction of the C+D ring motif of steroids to prepare series of novel secosteroids containing nitrile or disulfide functionalities. Key steps in synthesis of these novel steroid analogues are palladium-catalyzed cross-coupling reactions. All target compounds were characterized by comprehensive analysis; in particular the stereochemical assignments of dinitriles 12a and 12b could be carried out in detail by NMR experiments. The pharmacological potential of all compounds was initially verified by a cytotoxicity test.