Abstract
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 11β and 13β, respectively. The characteristic 1H and 13C NMR spectroscopic features of the synthesized steroids are reported.
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