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

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

doi:10.1016/j.steroids.2005.11.002

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

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

Strathclyde Institute Of Pharmacy And Biomedical Sciences

Research output: Contribution to journal › Article › peer-review

7 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 language	English
Pages (from-to)	266-272
Number of pages	7
Journal	Steroids
Volume	71
Issue number	3
Early online date	20 Dec 2005
DOIs	https://doi.org/10.1016/j.steroids.2005.11.002
Publication status	Published - 31 Mar 2006

Keywords

chromatography, thin layer
ketones
molecular structure
sterioids

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10.1016/j.steroids.2005.11.002

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

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.",

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year = "2006",

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doi = "10.1016/j.steroids.2005.11.002",

language = "English",

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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.

PY - 2006/3/31

Y1 - 2006/3/31

N2 - 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.

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.

KW - chromatography, thin layer

KW - ketones

KW - molecular structure

KW - sterioids

UR - http://www.sciencedirect.com/science/article/pii/S0039128X05002588

U2 - 10.1016/j.steroids.2005.11.002

DO - 10.1016/j.steroids.2005.11.002

M3 - Article

C2 - 16368121

SN - 0039-128X

VL - 71

SP - 266

EP - 272

JO - Steroids

JF - Steroids

IS - 3

ER -

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

Abstract

Keywords

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