Conjugate hydrocyanation of 17-acetyl-11-carbomethoxygona-1,3,5(10),13(17)-tetraenes.

The conjugate hydrocyanation of 17-acetylgona-11-carbomethoxy-1,3,5(10),13(17)-tetraenes using diethylaluminum cyanide (Nagata reaction) is reported. This methodology has allowed the introduction of an angular cyano group at the C-13 position of the steroid skeleton. Subsequent reduction of the nitrile group yielded various functionalized steroids. One of them, 22 bears the natural trans/anti/trans stereochemistry and possesses an hydroxyl and aminomethyl functionalities in the positions 11beta and 13beta, respectively. The characteristic (1)H and (13)C NMR spectroscopic features of the synthesized steroids are reported.