The synthesis of A- and B-ring fluorinated analogues of cholesterol

Michael G. Thomas; Colin J. Suckling; Andrew R. Pitt; Keith E. Suckling

doi:10.1039/a904826j

The synthesis of A- and B-ring fluorinated analogues of cholesterol

Michael G. Thomas, Colin J. Suckling, Andrew R. Pitt, Keith E. Suckling^*

^*Corresponding author for this work

Analytical, Measurements and Physical Chemistry

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

Abstract

The synthesis of a number of mono- and difluorinated steroids with the potential to act as probes of the metabolism of cholesterol is described. 2ct-FluorochoIestan-3-one 7,4-fiuorocholest-5-en-3-one 11 and 6-fluorocholest-4-en-3one 12 were synthesised from the appropriate silyl enol ethers using 1-fluoropyridinium triflate, and subsequently reduced to the corresponding alcohols, 8,13 and 14 respectively. A similar approach was used to synthesise 2,2difiuorocholestan-3-ol 16 starting from the monofluoro steroid 7. To synthesise 4,4-difiuorocholestan-3β-ol 26, 3β-acetoxycholestan-4-one 25 was generated via an acid catalysed rearrangement of 4,5-epoxycholestan-3-one 20 and treated with DAST. Finally, a difluorocyclopropyl analogue of cholesterol 28 was synthesised using chlorodifluoroacetic acid.

Original language	English
Pages (from-to)	3191-3198
Number of pages	8
Journal	Chemical Society. Journal. Perkin Transactions I
Issue number	21
DOIs	https://doi.org/10.1039/a904826j
Publication status	Published - 1999

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title = "The synthesis of A- and B-ring fluorinated analogues of cholesterol",

abstract = "The synthesis of a number of mono- and difluorinated steroids with the potential to act as probes of the metabolism of cholesterol is described. 2ct-FluorochoIestan-3-one 7,4-fiuorocholest-5-en-3-one 11 and 6-fluorocholest-4-en-3one 12 were synthesised from the appropriate silyl enol ethers using 1-fluoropyridinium triflate, and subsequently reduced to the corresponding alcohols, 8,13 and 14 respectively. A similar approach was used to synthesise 2,2difiuorocholestan-3-ol 16 starting from the monofluoro steroid 7. To synthesise 4,4-difiuorocholestan-3β-ol 26, 3β-acetoxycholestan-4-one 25 was generated via an acid catalysed rearrangement of 4,5-epoxycholestan-3-one 20 and treated with DAST. Finally, a difluorocyclopropyl analogue of cholesterol 28 was synthesised using chlorodifluoroacetic acid.",

author = "Thomas, {Michael G.} and Suckling, {Colin J.} and Pitt, {Andrew R.} and Suckling, {Keith E.}",

year = "1999",

doi = "10.1039/a904826j",

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pages = "3191--3198",

journal = "Chemical Society. Journal. Perkin Transactions I",

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publisher = "Royal Society of Chemistry",

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T1 - The synthesis of A- and B-ring fluorinated analogues of cholesterol

AU - Thomas, Michael G.

AU - Suckling, Colin J.

AU - Pitt, Andrew R.

AU - Suckling, Keith E.

PY - 1999

Y1 - 1999

N2 - The synthesis of a number of mono- and difluorinated steroids with the potential to act as probes of the metabolism of cholesterol is described. 2ct-FluorochoIestan-3-one 7,4-fiuorocholest-5-en-3-one 11 and 6-fluorocholest-4-en-3one 12 were synthesised from the appropriate silyl enol ethers using 1-fluoropyridinium triflate, and subsequently reduced to the corresponding alcohols, 8,13 and 14 respectively. A similar approach was used to synthesise 2,2difiuorocholestan-3-ol 16 starting from the monofluoro steroid 7. To synthesise 4,4-difiuorocholestan-3β-ol 26, 3β-acetoxycholestan-4-one 25 was generated via an acid catalysed rearrangement of 4,5-epoxycholestan-3-one 20 and treated with DAST. Finally, a difluorocyclopropyl analogue of cholesterol 28 was synthesised using chlorodifluoroacetic acid.

AB - The synthesis of a number of mono- and difluorinated steroids with the potential to act as probes of the metabolism of cholesterol is described. 2ct-FluorochoIestan-3-one 7,4-fiuorocholest-5-en-3-one 11 and 6-fluorocholest-4-en-3one 12 were synthesised from the appropriate silyl enol ethers using 1-fluoropyridinium triflate, and subsequently reduced to the corresponding alcohols, 8,13 and 14 respectively. A similar approach was used to synthesise 2,2difiuorocholestan-3-ol 16 starting from the monofluoro steroid 7. To synthesise 4,4-difiuorocholestan-3β-ol 26, 3β-acetoxycholestan-4-one 25 was generated via an acid catalysed rearrangement of 4,5-epoxycholestan-3-one 20 and treated with DAST. Finally, a difluorocyclopropyl analogue of cholesterol 28 was synthesised using chlorodifluoroacetic acid.

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DO - 10.1039/a904826j

M3 - Article

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JO - Chemical Society. Journal. Perkin Transactions I

JF - Chemical Society. Journal. Perkin Transactions I

IS - 21

ER -

The synthesis of A- and B-ring fluorinated analogues of cholesterol

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