Synthesis of 15α-Hydroxylated Dehydroepiandrosterone and Androstenediol

Abstract

The titled compounds (1, 2) have been prepared from dehydroepiandrosterone. Introduction of the hydroxyl group into the 15α-position was attained by hydroboration of the 14, 15-double bond with diborane and subsequent oxidation of the organoborane with alkaline hydrogen peroxide under the protection of the 5, 6-double bond as the 3, 5-cyclo structure. A simple method for regeneration of the 3β-hydroxy-Δ⁵-steroid from the 3, 5-cyclo derivative was also developed.