One-pot, high yield synthesis of alpha-ketols from Delta5-steroids

Jorge A.R. Salvador, Vânia M. Moreira, James R. Hanson, Rui A. Carvalho

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)266-272
Number of pages7
JournalSteroids
Volume71
Issue number3
Early online date20 Dec 2005
DOIs
Publication statusPublished - 31 Mar 2006

Keywords

  • chromatography, thin layer
  • ketones
  • molecular structure
  • sterioids

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