SYNTHESIS AND SELECTIVE CATALYTIC OXIDATION OF NEW DIMERIC STEROIDS

Khaled Q. Shawakfeh, Ahmad M. Al-Ajlouni and Abdelatif Ibdah
Department of Applied Chemical Science, Jordan University of Science and Technology,
P. O. Box 3030, Irbid 22110, Jordan

Abstract
New dimeric steroids were synthesized by reductive amination of the aldehyde of 3-oxopregn-4-ene-20b-carboxaldehyde and the ketone of stigmasterol and cholesterol, with 1,3-diaminopropane, 1,4-diaminobutane and 1,6-diaminohexane  using sodium triacetoxyborohydride.  The catalytic oxidation of the double bond in these dimeric steroids by CH3ReO3/H2O2 system was carried out.  In the case of stigmasterol dimer 6, only the internal double bond was oxidized.