Application of ring-closing metathesis to the synthesis of 19-functionalized derivatives of 1α-hydroxyvitamin D3

Organic Letters

Volumn 8, Issue 5, 2006, Pages 839-842

  Wojtkielewicz, Agnieszka ^a   Morzycki, Jacek W ^a  

^a UNIVERSITY OF BIALYSTOK   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

COLECALCIFEROL; DRUG DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CHOLECALCIFEROL; CYCLIZATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 33644935025     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052856k     Document Type: Article

References (19)

1. Holick, M. F., Ed. Vitamin D: Physiology, Molecular Biology and Clinical Aplications; Humana Press: Totowa, NJ, 1999.
2. (a) Bouillon, R. M.; Okamura, W. H.; Norman, A. W. Endocr. Rev. 1995, 16, 200.
3. (b) Muralidharan, K. R.; De Lera, A. R.; Isaeff, S. D.; Norman, A. W.; Okamura, W. H. J. Org. Chem. 1993, 58, 1895.
4. (c) Perlman, K. L.; Sicinski, R. R.; Schnoes, H. K.; DeLuca, H. F. Tetrahedron Lett. 1990, 31, 1823.
5. (d) Kanzler, S.; Halkes, S.; van de Velde, J. P.; Reischel, W. Bioorg. Med. Chem. Lett. 1996, 6, 1865.
6. (e) Kroszczynski, W.; Morzycka, B.; Morzycki, J. W. Wiad. Chem. 2002, 56, 793.
7. (a) Yamada, S.; Nakayama, K.; Takayama, H.; Itai, A.; Iitaka, Y. J. Org. Chem. 1983, 48, 3477.
8. (b) Yamada, S.; Suzuki, T.; Takayama, H. J. Org. Chem. 1983, 48, 3483.
9. (c) Addo, J. K.; Ray, R. Steroids 1998, 63, 218.
10. (d) Swamy, N.; Addo, J. K.; Ray, R. Bioorg. Med. Chem. Lett. 2000, 10, 361.
11. (e) Addo, J. K.; Swamy, N.; Ray, R. Bioorg. Med. Chem. Lett. 2002, 12, 279.
12. (f) Ahmed, M.; Atkinson, C. E.; Barrett, A. G. M.; Malagu, K.; Procopiou, P. A. Org. Lett. 2003, 5, 669.
13. (a) Grubbs, R. H. Tetrahedron 2004, 60, 7117.
14. (b) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199.
15. (c) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
16. 3) ester in dry toluene dropwise over 2 h. The reaction mixture was stirred at 80 °C for 4 h under argon atmosphere. Then the reaction mixture was concentrated in vacuo and purified by silica gel column chromatography.
17. Marshall, J. A.; Grote, J.; Shearer B. J. Org. Chem. 1986, 51, 1635.
18. Gielen, J. W. J.; Koolstra, R. B.; Jacobs, H. J. C.; Havinga, E. J. R. Neth. Chem. 1980, 99, 306.
19. Paaren, H. E.; DeLuca, H. F.; Schnoes, H. K. J. Org. Chem. 1980, 45, 3253.