Collect. Czech. Chem. Commun. 1996, 61, 1655-1661

Improved Methods for Obtaining Immonium Perchlorates and Enamines of Solanidine Type Steroidal Alkaloids

Katarina M. Penov Gašia, Dušica Rackov Čolica, Otto N. Arcsona, Zvonimir O. Sakača, Evgenija A. Djurendića, Marija N. Sakača, Ljubica Medic-Mijačevicb and Dušan A. Miljkovića

a Institute of Chemistry, Faculty of Sciences, Trg Dositeja Obradovića 3, 21000 Novi Sad, Yugoslavia
b ICN Galenika, Institute, 29. Novembar 111, 11000 Beograd, Yugoslavia


Oxidation of solanidine and some of its derivatives with mercury(II) acetate in acetone afforded corresponding N-22 immonium perchlorates or 22(23)-enamines. It has been found that the effect of solvents on regioselectivity e.g. formation N-22 and N-16 immonium salts, was remarkable. The isomerisation of 22(23)-enamines into corresponding 20(22)-enamines, potentialy important intermediates in planned chemical degradation of solanidine to steroidal hormones, was performed in 0.1% acetic acid in ether, or in dichloromethane (chloroform).

Keywords: Steroidal alkaloids; Solanidine; N-22 Immonium perchlorates; Enamines.