Synthetic approach to analogues of 19-norsteroids with an acyclic side chain

Racemic 14 beta-hydroxy-3-methoxy-8 alpha,9 alpha-1,3,5(10)-estratriene-17-one (I), obtained by total synthesis, was converted into a derivative with alkoxycarbonyl-ethylenic side chain, rac-(20E)-21-methoxycarbonyl-19-nor-8 alpha,9 alpha-pregna- 1,3,5(10),20-tetraene-3,14 beta-diol 3-methyl ether (XII) using two Wittig reactions. Analogous derivatives of 5 alpha-androstane were prepared as synthetic models. In the estrane series the stereochemistry of attachement of the side chain in position 17, biological activity of some compounds, and their chromatographic properties were investigated.