Novel synthetic approach to 19-nor-1α,25-dihydroxyvitamin D3 and its derivatives by Suzuki-Miyaura coupling in solution and on solid support

Organic Letters

Volumn 3, Issue 24, 2001, Pages 3975-3977

  Hanazawa, Takeshi ^a   Wada, Takeshi ^a   Masuda, Tomoko ^a   Okamoto, Sentaro ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,25 DIHYDROXY 19 NORVITAMIN D3; 1,25-DIHYDROXY-19-NORVITAMIN D3; CALCITRIOL; DRUG DERIVATIVE;

ARTICLE; CHEMISTRY; SOLUTION AND SOLUBILITY; SYNTHESIS;

CALCITRIOL; SOLUTIONS;

EID: 0035969599     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016908r     Document Type: Article

References (42)

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23. 5g
24. The reaction gave a mixture of the epoxyketone having the structure shown in Scheme 2 and its diastereomer in a ratio of >96:4, recrystallization of which from hexane provided the diastereomerically pure compound.
25. 1H NMR analyses, after converting to the corresponding MTPA esters, to be >99%.
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27. See Supporting Information.
28. Authentic sample of the cis isomer of 1 was prepared from 3 and 8, see Supporting Information.
29. Trost, B. M.; Dumas, J.; Villa, M. J. Am. Chem. Soc. 1992, 114, 9836.
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31. 3s, see: Doi, T.; Hijikuro, I.; Takahashi, T. J. Am. Chem. Soc. 1999, 121, 6749. Hijikuro, I.; Doi, T.; Takahashi, T. J. Am. Chem. Soc. 2001, 123, 3716.
32. 3s, see: Doi, T.; Hijikuro, I.; Takahashi, T. J. Am. Chem. Soc. 1999, 121, 6749. Hijikuro, I.; Doi, T.; Takahashi, T. J. Am. Chem. Soc. 2001, 123, 3716.
33. 3s, see: Doi, T.; Hijikuro, I.; Takahashi, T. J. Am. Chem. Soc. 1999, 121, 6749. Hijikuro, I.; Doi, T.; Takahashi, T. J. Am. Chem. Soc. 2001, 123, 3716.
34. Prepared from PS-DES (Argonaut Technologies) by the reported procedure: Hu. Y.; Porco, J. A., Jr.; Labadie, J. W.; Gooding, O. W.; Trost, B. M. J. Org. Chem. 1998, 63, 4518.
35. 11
36. 11
37. 1H NMR and HPLC analyses to be >95%.
38. 3s. Reviews on the synthesis and structure-function relationship of vitamin D analogues: Bouillon, R.; Okamura, W. H.; Norman, A. W. Endocr Rev. 1995, 16, 200. Zhu, G.-D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877. Dai, H.; Posner, G. H. Synthesis 1994, 1383. Uskokoovic, M., Ed. Bioorg. Med. Chem. Lett. 1993, 3(9), special issue.
39. 3s. Reviews on the synthesis and structure-function relationship of vitamin D analogues: Bouillon, R.; Okamura, W. H.; Norman, A. W. Endocr Rev. 1995, 16, 200. Zhu, G.-D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877. Dai, H.; Posner, G. H. Synthesis 1994, 1383. Uskokoovic, M., Ed. Bioorg. Med. Chem. Lett. 1993, 3(9), special issue.
40. 3s. Reviews on the synthesis and structure-function relationship of vitamin D analogues: Bouillon, R.; Okamura, W. H.; Norman, A. W. Endocr Rev. 1995, 16, 200. Zhu, G.-D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877. Dai, H.; Posner, G. H. Synthesis 1994, 1383. Uskokoovic, M., Ed. Bioorg. Med. Chem. Lett. 1993, 3(9), special issue.
41. 3s. Reviews on the synthesis and structure-function relationship of vitamin D analogues: Bouillon, R.; Okamura, W. H.; Norman, A. W. Endocr Rev. 1995, 16, 200. Zhu, G.-D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877. Dai, H.; Posner, G. H. Synthesis 1994, 1383. Uskokoovic, M., Ed. Bioorg. Med. Chem. Lett. 1993, 3(9), special issue.
42. 3c because the corresponding sulfone reagent might undergo elimination of an alkoxy group by treatment with a base.