One-pot, high yield synthesis of α-ketols from Δ5-steroids

α-Hydroxy ketones (α-ketols) are present in many compounds with biological activity. Several methods are available for the preparation of α-ketols but only a few of them describe the synthesis of steroid α-ketols from olefins. In this work, a new system consisting of KMnO4/Fe(ClO4)3·nH2O was used in order to achieve the direct conversion of Δ5-steroids to their corresponding α-ketols, in high yields. Consideration of the probable reaction mechanism is provided. 2D homo- and heteronuclear correlation NMR spectroscopic techniques were used to assign 1H and 13C resonances of some synthesized compounds. This method has potential for the preparation of α-hydroxy ketones of biological interest.