- Synthesis of 24-functionalized oxysterols
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The syntheses of (24S)-24,25-epoxycholesterol, (24S)-hydroxycholesterol, and 24-ketocholesterol are described. The compounds belong to oxysterols, which can be considered to be the modulators of cholesterol metabolism. The asymmetric hydroxylation of desmosterol acetate according to Sharpless was used as the key reaction in the stereoselective introduction of functionality in position 24.
- Khripach,Zhabinskii,Konstantinova,Khripach,Antonchick
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p. 257 - 261
(2007/10/03)
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- Stereocontrolled syntheses of 24(S),25-epoxycholesterol and related oxysterols for studies on the activation of LXR receptors
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Efficient syntheses are described of desmosterol (4), the corresponding 24(S),25 epoxide (6) and various analogs of 6 for evaluation as ligands and functional activators of LXR receptors.
- Corey,Grogan, Michael J.
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p. 9351 - 9354
(2007/10/03)
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- Efficient, stereoselective synthesis of 24(s), 25-epoxycholesterol
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Efficient, stereoselective syntheses of 24(S), 25-epoxycholesterol (1) have been developed starting from cholenic acid (4) or stigmasterol (8), both featuring as the key step Sharpless asymmetric dihydroxylation of desmosterol acetate (2). This work permits preparation of gram quantities of 1 for further evaluation as a natural regulator of cholesterol metabolism, specifically, e.g., as a ligand for the LXRα. nuclear receptor.
- Tomkinson, Nicholas C. O.,Willson, Timothy M.,Russel, Jonathon S.,Spencer, Thomas A.
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p. 9919 - 9923
(2007/10/03)
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