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

Tomkinson, Nicholas C. O. and Willson, Timothy M. and Spencer, Thomas A. and Russell, Jonathon S. (1998) Efficient, stereoselective synthesis of 24(S),25-epoxycholesterol. In: 216th National Meeting of the American Chemical Society, 1998-08-23 - 1998-08-27.

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Efficient, stereoselective syntheses of 24(S),25-epoxycholesterol (1) have been developed starting from cholenic acid (2) or stigmasterol (3), both featuring as the key step Sharpless asym. dihydroxylation of desmosterol acetate (4). This work permits prepn. of gram quantities of 1 for further evaluation as a natural regulator of cholesterol metab., specifically, e.g., as a ligand for the LXRα nuclear receptor. [on SciFinder(R)]