19-Nordehydroepiandrosterone
19-Nordehydroepiandrosterone, or 19-nor-5-dehydroepiandrosterone, is an estrane steroid which was never marketed. It is the combined derivative of the androgen/anabolic steroid nandrolone and the androgen prohormone dehydroepiandrosterone. Related compounds include 19-nor-5-androstenediol, bolandiol, and bolandione, which are all known orally active prohormones of nandrolone. 19-Nor-DHEA may occur as a metabolite of bolandione and related steroids.
Synthesis
The chemical synthesis of 19-Nordehydroepiandrosterone was reported.The enone group in Bolandione is protected with isopropenyl acetate to give the corresponding enol acetate . Ketalization of the remaining carbonyl with ethyleneglycol in the presence of triethyl orthoformate gives. Reduction of the enol ether by treatment with sodium borohydride occurred to give . Hydrolytic removal of the cyclic ketal in weak acid completed the synthesis of 19-Nor-DHEA.