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

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

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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

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