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

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

doi:10.1021/JO981753V

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

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

Pure And Applied Chemistry

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

40 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 language	Undefined/Unknown
Pages (from-to)	9919-9923
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	63
Issue number	26
DOIs	https://doi.org/10.1021/JO981753V
Publication status	Published - 1998

Keywords

stereoselective synthesis
25-epoxycholesterol
cholesterol

Access to Document

10.1021/JO981753V

Cite this

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

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. ",

keywords = "stereoselective synthesis , 25-epoxycholesterol, cholesterol ",

author = "Tomkinson, {Nicholas C. O.} and Willson, {Timothy M.} and Russel, {Jonathon S.} and Spencer, {Thomas A.}",

year = "1998",

doi = "10.1021/JO981753V",

language = "Undefined/Unknown",

volume = "63",

pages = "9919--9923",

journal = "Journal of Organic Chemistry",

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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

SN - 0022-3263

VL - 63

SP - 9919

EP - 9923

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 26

ER -