Synthesis of 9-alkylated calcitriol and two 1α,25-dihydroxy-9- methylene-10,19-dihydrovitamin D3 analogues with a non-natural triene system by thermal sigmatropic rearrangements

Journal of Organic Chemistry

Volumn 78, Issue 4, 2013, Pages 1444-1450

  Kulesza, Urszula ^a   Sigüeiro, Rita ^b   Mouriño, Antonio ^b   Sicinski, Rafal R ^a  

^a UNIVERSITY OF WARSAW   (Poland)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL SUBSTITUENT; ALTERNATIVE APPROACH; HYDROGEN SHIFTS; METHYL GROUP; NATURAL HORMONE; PROPARGYL ALCOHOL; SIGMATROPIC REARRANGEMENTS; STEREO-SELECTIVE; THERMAL ISOMERIZATIONS;

CHEMISTRY; ORGANIC COMPOUNDS;

FUNCTIONAL GROUPS;

ALCOHOL; CALCITRIOL DERIVATIVE; COLECALCIFEROL DERIVATIVE; HYDROGEN; METHYL GROUP;

ARTICLE; CHEMICAL STRUCTURE; ISOMERIZATION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

ALKANES; ALKYLATION; CALCITRIOL; HYDROXYCHOLECALCIFEROLS; METHANE; MOLECULAR STRUCTURE;

EID: 84873979386     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302513e     Document Type: Article

References (43)

1. Feldman, D., Pike, J. W., Glorieux, F. H., Eds. Vitamin D, 2 nd ed.; Elsevier Academic Press: Burlington, MA, 2005.
2. Feldman, D., Pike, J. W., Adams, J. S., Eds. Vitamin D, 3 rd ed.; Elsevier Academic Press: San Diego, CA, 2011.
3. Pike, J. W.; Meyer, M. B.; Bishop, K. A. Rev. Endocr. Metab. Dis. 2012, 13, 45-55
4. Campbell, M. J.; Adorini, L. Expert Opin. Ther. Targets 2006, 10, 735-748
5. Carlberg, C.; Quack, M.; Herdick, M.; Bury, Y.; Polly, P.; Toell, A. Steroids 2001, 66, 213-221
6. Evans, R. M. Science 1988, 240, 889-895
7. Evans, R. M. Mol. Endocrinol. 2005, 19, 1429-1438
8. Jones, G.; Strugnell, S. A.; DeLuca, H. F. Physiol. Rev. 1998, 78, 1193-1231
9. Holick, M. F.; MacLaughlin, J. A.; Doppelt, S. H. Science 1981, 211, 590-593
10. Hanewald, K. H.; Rappoldt, M. P.; Roborgh, J. R. Recl. Trav. Chim. Pays-Bas. 1961, 80, 1003-1014
11. Woodward, R. B.; Hoffman, R. J. Am. Chem. Soc. 1965, 87, 2511-2513
12. Woodward, R. B.; Hoffman, R. Angew. Chem. 1969, 81, 797-869
13. Havinga, E.; de Kock, R. J.; Rappoldt, M. P. Tetrahedron 1960, 11, 276-284
14. Havinga, E.; Schlatmann, J. L. M. A. Tetrahedron 1961, 16, 146-152
15. Havinga, E. Chimia 1962, 16, 145-151
16. Schlatmann, J. L. M. A.; Pot, J.; Havinga, E. Recl. Trav. Chim. Pays-Bas 1964, 83, 1173-1184
17. Havinga, E. Experientia 1973, 29, 1181-1316
18. Akhtar, M.; Gibbons, C. J. Tetrahedron Lett. 1965, 6, 509-512
19. Akhtar, M.; Gibbons, C. J. J. Chem. Soc. 1965, 5964-5968
20. Sheves, M.; Berman, E.; Mazur, Y.; Zaretskii, Z. J. Am. Chem. Soc. 1979, 101, 1882-1883
21. Moriarty, R. M.; Paaren, H. E. Tetrahedron Lett. 1980, 21, 2389-2392
22. Spangler, C. W. Chem. Rev. 1976, 76, 187-217
23. Hoeger, C. A.; Okamura, W. H. J. Am. Chem. Soc. 1985, 107, 268-270
24. Hoeger, C. A.; Johnston, A. D.; Okamura, W. H. J. Am. Chem. Soc. 1987, 109, 4690-4698
25. Zhu, G. D.; Okamura, W. H. Endocr. Rev. 1995, 95, 1877-1957
26. Nagpal, S.; Na, S. Q.; Rathnachalam, R. Endocr. Rev. 2005, 26, 662-687
27. Maestro, M. A.; Sardina, J. F.; Castedo, L.; Mouriño, A. J. Org. Chem. 1991, 56, 3582-3587
28. An alternative procedure for such α-methylation described in the Japanese patent for an analogous MEM-protected hydroxy ketone was significantly less efficient: Shimizu, M. 9-Substituted-19-norvitamin D Derivative. WIPO Patent Application WO/2006/093290.
29. Sicinski, R. R.; Perlman, K. L.; DeLuca, H. F. J. Med. Chem. 1994, 37, 3730-3738
30. Castedo, L.; Mascareñas, J. L.; Mouriño, A. Tetrahedron Lett. 1987, 28, 2099-2102
31. Aurrecoechea, J. M.; Okamura, W. H. Tetrahedron Lett. 1987, 28, 4947-4950
32. Okamura, W. H.; Aurrecoechea, J. M.; Gibbs, R. A.; Norman, A. W. J. Org. Chem. 1989, 54, 4072-4083
33. Barton, D. H. R.; Bashiardes, G.; Fourrey, J.-L. Tetrahedron Lett. 1983, 24, 1605-1608
34. Castedo, L.; Mouriño, A.; Sarandeses, L. Tetrahedron Lett. 1986, 27, 1523-1526
35. Mascareñas, J. L.; Sarandeses, L. A.; Castedo, L.; Mouriño, A. Tetrahedron 1991, 47, 3485-3489
36. Scott, W. J.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630-4632
37. Sheves, M.; Mazur, Y. J. Chem. Soc., Chem. Commun. 1977, 21-22
38. Burgess, E. M.; Penton, H. R., Jr.; Taylor, E. A. J. Org. Chem. 1973, 38, 26-31
39. Sicinski, R. R.; Perlman, K. L.; Prahl, J.; Smith, C.; DeLuca, H. F. J. Med. Chem. 1996, 39, 4497-4506
40. Johnson, F.; Malhotra, S. K. J. Am. Chem. Soc. 1965, 87, 5492-5493
41. Johnson, F. Chem. Rev. 1968, 68, 375-413
42. Nasipuri, D. Stereochemistry of Organic Compounds; Wiley Eastern: New Delhi, 1991; pp 270-271.
43. Sicinski, R. R.; DeLuca, H. F. Bioorg. Chem. 1994, 22, 150-171