Simple, stereocontrolled syntheses of 24(S),25-epoxy-22(R)- hydroxycholesterol, 22(R),24(S)-dihydroxycholesterol and diastereomers, new ligands for binding and activation of LXRs

Tetrahedron Letters

Volumn 39, Issue 51, 1998, Pages 9355-9356

  Corey, E J ^a   Grogan, Michael J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

22 HYDROXYCHOLESTEROL; CELL NUCLEUS RECEPTOR; CHOLESTEROL DERIVATIVE; EPOXIDE;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; EPOXIDATION; HYDROXYLATION; LIGAND BINDING; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EID: 0032542127     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02182-0     Document Type: Article

References (15)

1. 1. Janowski, B. A.; Willy, P. J.; Devi, T. R.; Falck, J. R.; Mangelsdorf, D. J. Nature 1996, 383, 728.
2. 2. Lehmann, J. M.; Kliewer, S. A.; Moore, L. B.; Smith-Oliver, T. A.; Oliver, B. B.; Su, J.-L.; Sundseth, S. S.; Winegar, D. A.; Blanchard, D. E.; Spencer, T. A.; Willson, T. M. J. Biol. Chem. 1997, 272, 3137.
3. 3. Lutjohann, D.; Breuer, O.; Ahlborg, G.; Nennesmo, I.; Siden, A.; Diczfalusy, U.; Bjorkhem, I. Proc. Natl. Acad. Sci. 1996, 93, 9799.
4. 4. Corey, E. J.; Grogan, M. J. Tetrahedron Letters 1998, 39, 9351.
5. 5. Corey, E. J.; Gross, S. K. J. Am. Chem. Soc. 1967, 89, 4561.
6. 6. Spencer, T. A. Acc. Chem. Res. 1994, 27, 83.
7. 7. Janowski, B. A.; Grogan, M. J.; Jones, S. A.; Kliewer, S. A.; Corey, E. J.; Mangelsdorf, D. J. Proc. Natl. Acad. Sci. USA submitted.
8. 8. Zhou, W.-S.; Jiang, B.; Pan, X.-F. Tetrahedron 1990, 46, 3173.
9. 9. Evans, D. A.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190.
10. 10. Mihelich, E. D.; Daniels, K.; Eickhoff, D. J. J. Am. Chem. Soc. 1981, 103, 7690.
11. 11. Yanagisawa, A.; Habaue, S.; Yasue, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6130.
12. 12. Anh, N. T.; Eisenstein, O. Nov. J. Chim. 1977, 1, 61; Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Letters 1968, 2199.
13. 12. Anh, N. T.; Eisenstein, O. Nov. J. Chim. 1977, 1, 61; Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Letters 1968, 2199.
14. 1[I>2σ(I)] = 0.0459.
15. 14. This work was supported by a grant from the National Institutes of Health and a predoctoral fellowship for MJG from Eli Lily and Co.