One-pot, high yield synthesis of alpha-ketols from Delta5-steroids.
Alpha-hydroxy ketones (alpha-ketols) are present in many compounds with biological activity. Several methods are available for the preparation of alpha-ketols but only a few of them describe the synthesis of steroid alpha-ketols from olefins. In this work, a new system consisting of KMnO(4)/Fe(ClO(4))(3).nH(2)O was used in order to achieve the direct conversion of Delta(5)-steroids to their corresponding alpha-ketols, in high yields. Consideration of the probable reaction mechanism is provided. 2D homo- and heteronuclear correlation NMR spectroscopic techniques were used to assign (1)H and (13)C resonances of some synthesized compounds. This method has potential for the preparation of alpha-hydroxy ketones of biological interest.
Salvador
Jorge A R
JA
Laboratório de Química Farmacêutica, Faculdade de Farmácia, Universidade de Coimbra, Rua do Norte, 3000-295 Coimbra, Portugal. salvador@ci.uc.pt
Moreira
Vânia M
VM
Hanson
James R
JR
Carvalho
Rui A
RA
D002855:Chromatography, Thin Layer; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013256:Steroids / Q000737:chemistry*
D007659:Ketones; D013256:Steroids