Collect. Czech. Chem. Commun. 1979, 44, 1619-1629

Deoxygenation at the carbon C(5) of 3,6-cyclo-A-nor-3,5-secoandrostanes

Alexander Kasal

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Attempted hydrogenolysis of methanesulfonate VIII led to products of elimination and rearrangement only. On treatment with ethanedithiol the hydroxy ketone VI yielded dithiolane derivative XXIV besides the product of retroaldol reaction, XXIII. Desulfurization of XXIV with Raney nickel followed by standard chemical transformations led to the desired analogues of testosterone, androstenedione and androsterone (XXIX-XXXI).