Efficient, stereoselective synthesis of 24(S),25-epoxycholesterol

Nicholas C. O. Tomkinson, Timothy M. Willson, Jonathon S. Russel, Thomas A. Spencer

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

Efficient, stereoselective syntheses of 24(S),25-epoxycholesterol (I) have been developed starting from cholenic acid or stigmasterol, both featuring as the key step Sharpless asym. dihydroxylation of desmosterol acetate. This work permits prepn. of gram quantities of I for further evaluation as a natural regulator of cholesterol metab., specifically, e.g., as a ligand for the LXRα nuclear receptor.
Original languageUndefined/Unknown
Pages (from-to)9919-9923
Number of pages5
JournalJournal of Organic Chemistry
Volume63
Issue number26
DOIs
Publication statusPublished - 1998

Keywords

  • stereoselective synthesis
  • 25-epoxycholesterol
  • cholesterol

Cite this

Tomkinson, Nicholas C. O. ; Willson, Timothy M. ; Russel, Jonathon S. ; Spencer, Thomas A. / Efficient, stereoselective synthesis of 24(S),25-epoxycholesterol. In: Journal of Organic Chemistry. 1998 ; Vol. 63, No. 26. pp. 9919-9923.
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Efficient, stereoselective synthesis of 24(S),25-epoxycholesterol. / Tomkinson, Nicholas C. O.; Willson, Timothy M.; Russel, Jonathon S.; Spencer, Thomas A.

In: Journal of Organic Chemistry, Vol. 63, No. 26, 1998, p. 9919-9923.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Efficient, stereoselective synthesis of 24(S),25-epoxycholesterol

AU - Tomkinson, Nicholas C. O.

AU - Willson, Timothy M.

AU - Russel, Jonathon S.

AU - Spencer, Thomas A.

PY - 1998

Y1 - 1998

N2 - Efficient, stereoselective syntheses of 24(S),25-epoxycholesterol (I) have been developed starting from cholenic acid or stigmasterol, both featuring as the key step Sharpless asym. dihydroxylation of desmosterol acetate. This work permits prepn. of gram quantities of I for further evaluation as a natural regulator of cholesterol metab., specifically, e.g., as a ligand for the LXRα nuclear receptor.

AB - Efficient, stereoselective syntheses of 24(S),25-epoxycholesterol (I) have been developed starting from cholenic acid or stigmasterol, both featuring as the key step Sharpless asym. dihydroxylation of desmosterol acetate. This work permits prepn. of gram quantities of I for further evaluation as a natural regulator of cholesterol metab., specifically, e.g., as a ligand for the LXRα nuclear receptor.

KW - stereoselective synthesis

KW - 25-epoxycholesterol

KW - cholesterol

U2 - 10.1021/JO981753V

DO - 10.1021/JO981753V

M3 - Article

VL - 63

SP - 9919

EP - 9923

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 26

ER -