Novel synthesis of 1α,25-dihydroxy-19-norvitamin D from 25-hydroxyvitamin D

Tetrahedron

Volumn 65, Issue 48, 2009, Pages 10002-10008

  Toyoda, Asako ^a   Nagai, Hazuki ^a   Yamada, Tomonari ^a   Moriguchi, Yusuke ^b   Abe, Junko ^b   Tsuchida, Toshio ^a   Nagasawa, Kazuo ^b  

^a Mercian Bioresource Laboratories   (Japan)

^b TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1ALPHA,25 DIHYDROXY 19 NORVITAMIN D3; 25 HYDROXYERGOCALCIFEROL; ALKENE; PARICALCITOL; UNCLASSIFIED DRUG; VITAMIN D DERIVATIVE;

ARTICLE; BIOTRANSFORMATION; DRUG SYNTHESIS; HYDROBORATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 70350461485     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.09.115     Document Type: Article

References (36)

1. Bouillon R., Okamura W.H., and Norman A.W. Endocr. Rev. 16 (1995) 200
2. Jones G., Strugnell S.A., and DeLuca H.F. Physiol. Rev. 78 (1998) 1193
3. Yang S., Smith C., and DeLuca H.F. Biochim. Biophys. Acta 1158 (1993) 279
4. Robinson D.M., and Scott L.J. Drugs 65 (2005) 559
5. Direct synthesis for 3b, see:. Parlman K.L., Sicinski R.R., Schnoes H.K., and DeLuca H.F. Tetrahedron Lett. 31 (1990) 1823
6. Indirect synthesis for 3b, see:
7. Parlman K.L., Swenson R.E., Paaren H.E., Schnoes H.K., and DeLuca H.F. Tetrahedron Lett. 32 (1991) 7663
8. Ono Y., Kashiwagi H., and Takahashi T. Synth. Commun. 36 (2006) 1141
9. Hanazawa T., Wada T., Masuda T., Okamoto S., and Sato F. Org. Lett. 3 (2001) 3975
10. Huang P., Sabbe K., Pottie M., and Vandewalle M. Tetrahedron Lett. 36 (1995) 8299
11. Zhou S., Anné S., and Vandewalle M. Tetrahedron Lett. 37 (1996) 7637
12. Yong W., and Vandewalle M. Synlett (1996) 911
13. Recent direct synthesis of the other vitamin D derivatives, see:
14. Inaba Y., Yoshimoto N., Sakamaki Y., Nakabayashi M., Ikura T., Tamamura H., Ito N., Shimizu M., and Yamamoto K. J. Med. Chem. 52 (2009) 1438
15. Okabe M. Org. Synth. 76 (1999) 275 Indirect synthesis of 19-norvitamin D derivatives, see:
16. Shimizu M., Miyamoto Y., Takaku H., Matsuo M., Nakabayashi M., Masuno H., Udagawa N., DeLuca H.F., Ikura T., and Ito N. Bioorg. Med. Chem. 16 (2008) 6949
17. Glebocka A., Sokolowska K., Sicinski R.R., Plum L.A., and DeLuca H.F. J. Med. Chem. 52 (2009) 3496
18. Yoshida A., Ono K., Suhara Y., Saito N., Takayama H., and Kittaka A. Synlett (2003) 1175
19. Ono K., Yoshida A., Saito N., Fujishima T., Honzawa S., Suhara Y., Kishimoto S., Sugiura T., Waku K., Takayama H., and Kittaka A. J. Org. Chem. 68 (2003) 7407
20. Paaren H.E., DeLuca H.F., and Schnoes H.K. J. Org. Chem. 48 (1983) 3819
21. Paaren H.E., Schnoes H.K., and DeLuca H.F. J. Org. Chem. 45 (1980) 3253
22. Takeda K., Asou T., and Matsuda A. J. Ferment. Bioeng. 78 (1994) 380
23. Rubottom G.M., Vazquez M.A., and Pelegrina D.R. Tetrahedron Lett. 15 (1974) 4319 Stereochemistry at C1 could not be determined at this stage
24. Representative reaction conditions;
25. 2O, KOH, ethylene glycol, 150 °C;
26. 2O, tert-BuOK, DMSO- tert-BuOH, 70 °C;
27. 2, EtOH, 70 °C.
28. Cacchi S., Morera E., and Ortar G. Org. Synth. 68 (1990) 138
29. McMurry J.E., and Scott W.J. Tetrahedron Lett. 24 (1983) 979
30. Scott W.J., Crisp G.T., and Stille J.K. J. Am. Chem. Soc. 106 (1984) 4630
31. Cacchi S., Morera E., and Ortar G. Tetrahedron Lett. 25 (1984) 4821
32. Scott W.J., and Stille J.K. J. Am. Chem. Soc. 108 (1986) 3033
33. Gilbertson S.R., Challener C.A., Bos M.E., and Wulff W.D. Tetrahedron Lett. 29 (1988) 4795
34. 12b
35. Ng, C.S.; Wei, C.P. US patent US2009/0149678A1.
36. Spectral data for 3b was supplied by Dr. Masato Shimizu.