Synthesis of Some Novel 3,3-Ethylenedioxyandrost-7β-Acyloxy-5-Ene-17-One Derivatives as Potent Aromatase Inhibitors

Abstract

3,3,17,17-Diethylenedioxyandrost-5-ene was obtained by ketalisation of androstenedione, which was oxidised with PDC and t-BuOOH to form 3,3,17,17-diethylene-dioxyandrost-5-ene-7-one. Stereoselective reduction of 3,3,17,17-diethylene-dioxyandrost-5-ene-7-one by NaBH4 in the presence of CeCl3.6H2O gave 3,3,17,17-diethylenedioxy-7β-hydroxy-androst-5-ene, which was deprotected with p-toluenesulfonic acid to gave 3,3-ethylenedioxyandrost-5-ene-7β-hydroxy and androst-4,6-dien-3,17-dione. A series of androstenedione derivatives were obtained from 3,3-ethylenedioxyandrost-5-ene-7β-hydroxy by the esterification reaction. Their structures were confirmed by MS, 1H NMR, 13C NMR and HRMS.