Collect. Czech. Chem. Commun. 1998, 63, 1549-1563

Hydrogenation of a Tetrasubstituted Double Bond: Synthesis of 5-Methyl-19-nor-5β-pregnanes

Alexander Kasal, Jiří Polman and Miloš Buděšínský

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic


Reduction of C=C and/or C=O bonds in 5-methyl-19-nor-5β-pregn-9-ene-3,20-dione (1) leads to saturated and unsaturated ketones and hydroxy ketones. The C=C reduction affords mainly 9β,10β and 9α,10β dihydro products. Reaction conditions of partial esterification, hydrolysis and oxidation were elaborated. Several analogues were prepared for the testing of gestagenic and neurosteroidal activities.

Keywords: Westphalen rearrangement; Partial acetylation; Partial oxidation; Partial hydrolysis; 1H NMR spectroscopy; Hydrogenolysis; Configuration; Steroids.