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.

LanguageEnglish
Pages266-272
Number of pages7
JournalSteroids
Volume71
Issue number3
Early online date20 Dec 2005
DOIs
Publication statusPublished - 31 Mar 2006

Fingerprint

Ketones
Steroids
Biomolecular Nuclear Magnetic Resonance
Alkenes
Bioactivity
Nuclear magnetic resonance
ferryl iron

Keywords

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

Cite this

Salvador, Jorge A.R. ; Moreira, Vânia M. ; Hanson, James R. ; Carvalho, Rui A. / One-pot, high yield synthesis of alpha-ketols from Delta5-steroids. In: Steroids. 2006 ; Vol. 71, No. 3. pp. 266-272.
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One-pot, high yield synthesis of alpha-ketols from Delta5-steroids. / Salvador, Jorge A.R.; Moreira, Vânia M.; Hanson, James R.; Carvalho, Rui A.

In: Steroids, Vol. 71, No. 3, 31.03.2006, p. 266-272.

Research output: Contribution to journalArticle

TY - JOUR

T1 - One-pot, high yield synthesis of alpha-ketols from Delta5-steroids

AU - Salvador, Jorge A.R.

AU - Moreira, Vânia M.

AU - Hanson, James R.

AU - Carvalho, Rui A.

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AB - 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.

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KW - molecular structure

KW - sterioids

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