Syntheses of 15α-Hydroxyestrone and 15α-Hydroxyestradiol

Abstract

15.alpha.-Hydroxyestrone [1] and 15.alpha.-hydroxyestradiol were prepared from estrone by the new synthetic routes. Introduction of a OH group into the 15.alpha.-position was readily attained by hydroboration of the 14,15- or 15,16-double bond with diborane and subsequent oxidation of the organoborane with alkaline hydrogen peroxide. In the preparation of 1 the dimethyltert-butylsilyl function was conveniently employed for the purpose of protecting the 3,17.beta.-hydroxyl groups.