Diastereoselective Addition of Organomagnesium Reagents to 17β-TBDMS-Dihydrotestosterone

Abstract

Several alkylations of the C3-carbonyl of 17p-TBDMS-DHT (1) with Grignard reagents were performed to obtain a series of potential inhibitors of androgen formation. It has been found that, depending on the nucleophilicity of the Grignard reagent used, there was a difference in the diastereoselectivity. The stronger reagents proceeded preferentially through the equatorial attack, while the weaker ones proceeded through the axial attack.