Synthesis of (25R)-cholest-5-ene-3β,26-diol and its radiolabeled analog

Tetrahedron Letters

Volumn 38, Issue 22, 1997, Pages 3801-3804

  D'Ambra, Thomas E ^a   Javitt, Norman B ^b   Nakanishi, Koji ^b   Warchol, Tadeusz ^a  

^a ALBANY MOLECULAR RESEARCH INC   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

CHOLEST 5 ENE 3BETA,26 DIOL; STEROL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOTOPE LABELING; SYNTHESIS;

TRITIUM;

EID: 0030915339     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00750-8     Document Type: Article

References (29)

1. According to recent nomenclature this compound is referred as 27-hydroxycholesterol. Popjak, G.; Edmond, J.; Anet, F. A. L.; Eaton, N. R.; Jr. J. Am. Chem. Soc. 1977, 99, 931-935.
2. Reviews: a). Javitt, N. B. J. Lipid Res. 1990, 31, 1527-1533.
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5. Javitt, N. B. et al. unpublished data.
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9. a). Arunachalam, T.; MacKoul, P. J. Green, N. M.; Caspi, E. J. Org. Chem. 1981, 46, 2966-2968.
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11. c). idem, ibid 1987, 1713-1718 (related 25S epimer from yamogenin).
12. d). Kim, H.-S.; Wilson, W. K.; Needleman, D. H.; Pinkerton, F. D.; Wilson, D. K.; Quiocho, F. A.; Schroepfer, G. J. Jr. J. Lipid Res. 1989, 30, 247-261.
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15. Responsible for C-25 epimerization is [1, 5]-H shift: Seo, S.; Uomori, A., Takeda, K. J. Org. Chem. 1986, 51, 3823-3827 and ref. 5b. For diastereopurity determination see: a). Redel, J.; Capilon, J. J. Chromat. 1978, 151, 418-420.
16. Responsible for C-25 epimerization is [1, 5]-H shift: Seo, S.; Uomori, A., Takeda, K. J. Org. Chem. 1986, 51, 3823-3827 and ref. 5b. For diastereopurity determination see: a). Redel, J.; Capilon, J. J. Chromat. 1978, 151, 418-420.
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18. c). Arunachalam, T.; Hodgin, J. C.; Caspi, E. ibid. 1986, 351, 604-607.
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23. For syntheses of isotope labeled 27-hydroxycholesterol see: Ni, Y.; Kim, H-S.; Wilson, W. K.; Kisic, A.; Schroepfer, G. J. Jr. J. Lipid. Res. 1993, 34, 3687-3690 and references cited therein.
24. Hutchins, R. F. N.; Thompson, M. J.; Svoboda, J. A. Steroids 1970, 15, 113-119.
25. D'Ambra, T. E.; Courts, L. D.; Geiss, W. B.; Opalka, C. J.; Malone, M. A.; Chen, J. L. unpublished results.
26. Review: Kocienski, P. Phosp. Sulphur 1985, 24, 97-127.
27. All compounds gave satisfactory spectroscopic and analytical data. Experimental details will be given further in the full account of this study.
28. Opposite enantiomers of compounds 8-11 have been described. Mori, K. Tetrahedron 1983, 39, 3107-3109.
29. Olefin 14 has two prochiral centers. C-22 and C-23. Tritiation yielded the 22, 23 diastereomeric mixture.