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Synthesis of 5-azaandrostane-3β, 17β-diol protected at the 17-hydroxyl group

Pavlović Vladimir D. (Faculty of Chemistry, Belgrade)
Dabović Milan M. (Center for Chemistry, ICTM, Belgrade, Serbia and Montenegro)
Martinović Saša (Center for Chemistry, ICTM, Belgrade, Serbia and Montenegro)
Lorenc Ljubinka B. (Faculty of Chemistry, Belgrade and Center for Chemistry, ICTM, Belgrade, Serbia and Montenegro)
Kalvoda Jaroslav (Leimgrubenweg, Binningen, Switzerland)

In the present paper, the preparation of 3β-hydroxy-17β-dimethyl-tert-butylsilyloxy- 5-azaandrostane (15) in fourteen steps is described. B-nor-17-oxoandrost- 5-en-3β-yl acetate (1)1,2 was used as the starting material, which was transformed to the key intermediate of the synthesis, B-nor-17β-dimethyl-tert-butylsilyloxyandrost- 4-en-3β-yl acetate (7).

Keywords: 5-azasteroids, B-nor-17-oxoandrost-5-en-3-yl acetate, 3β-hydroxy-17β-dimethyl-tert-butylsilyloxy-5-azaandrostane