Synthesis of C-19-functionalized 1α-hydroxyvitamin D2 analogues via ring-closing metathesis

Organic Letters

Volumn 5, Issue 5, 2003, Pages 669-672

  Ahmed, Mahmood ^a,b   Atkinson, Catherine E ^a,b   Barrett, Anthony G M ^a,b   Malagu, Karine ^a,b   Procopiou, Panayiotis A ^a,b  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DOXERCALCIFEROL; ERGOCALCIFEROL DERIVATIVE; FUNCTIONAL GROUP; ORGANOLITHIUM COMPOUND; REAGENT; 1 ALPHA HYDROXYERGOCALCIFEROL; 1 ALPHA-HYDROXYERGOCALCIFEROL; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ERGOCALCIFEROL; METALLOPORPHYRIN; ZINC;

ALLYLATION; ARTICLE; CYCLOADDITION; DIELS ALDER REACTION; DRUG SYNTHESIS; ELIMINATION REACTION; ENANTIOSELECTIVITY; REACTION ANALYSIS; RING CLOSING METATHESIS; SUBSTITUTION REACTION; TRANS ISOMER; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CYCLIZATION; ERGOCALCIFEROLS; INDICATORS AND REAGENTS; METALLOPORPHYRINS; STEREOISOMERISM; ZINC;

EID: 0038543271     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027406w     Document Type: Article

References (24)

1. Norman, A. W. Vitamin D the Calcium Homeostatic Steroid Hormone; Academic Press: New York, 1979.
2. (a) Zhou, J. Y.; Norman, A. W.; Chen, D. L.; Sun, G. W.; Uskokovic, M.; Koeffler, H. P. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 3929.
3. (b) Anzano, M. A.; Smith, J. M.; Uskokovic, M. R.; Peer, C. W.; Mullen, L. T.; Letterio, J. J.; Welsh, M. C.; Shrader, M. W.; Logsdon, D. L.; Driver, C. L.; Brown, C. C.; Roberts, A. B.; Sporn, M. B. Cancer Res. 1994, 54, 1653.
4. (c) Colston, K. W.; Chander, S. K.; Mackay, A. G.; Coombes, R. C. Biochem. Pharmacol. 1992, 44, 693.
5. Bouillon, R.; Okamura, W. H.; Norman, A. W. Endocr. Rev. 1995, 16, 200.
6. (a) Muralidharan, K. R.; De Lera, A. R.; Isaeff, S. D.; Norman, A. W.; Okamura, W. H. J. Org. Chem. 1993, 58, 1895.
7. (b) Perlman, K. L.; Sicinski, R. R.; Schnoes, H. K.; DeLuca, H. F. Tetrahedron Lett. 1990, 31, 1823.
8. (c) Kanzler, S.; Halkes, S.; van de Velde, J. P.; Reischl, W. Bioorg. Med. Chem. Lett. 1996, 6, 1865.
9. (a) Yamada, S.; Suzuki, T.; Takayama, H. Tetrahedron Lett. 1981, 22, 3085.
10. (b) Yamada, S.; Nakayama, K.; Takayama, H.; Itai, A.; Iitaka, Y. J. Org. Chem. 1983, 48, 3477.
11. (c) Addo, J. K.; Ray, R. Steroids 1998, 63, 218.
12. (d) Swamy, N.; Addo, J. K.; Ray, R. Bioorg. Med. Chem. Lett. 2000, 10, 361.
13. (e) Addo, J. K.; Swamy, N.; Ray, R. Bioorg. Med. Chem. Lett. 2002, 12, 279.
14. (a) Chang, S.; Grubbs, R. H. Tetrahedron Lett. 1997, 38, 4757.
15. (b) Meyer, C.; Cossy, J. Tetrahedron Lett. 1997, 38, 7861.
16. Micalizio, G. C.; Schreiber, S. L. Angew. Chem., Int. Ed. 2002, 41, 152.
17. (a) Andrews, D. R.; Barton, D. H. R.; Cheng, K. P.; Finet, J. P.; Hesse, R. H.; Johnson, G.; Pechet, M. M. J. Org. Chem. 1986, 51, 1635.
18. (b) Calverley, M. J. Tetrahedron 1987, 43, 4609.
19. Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694.
20. (a) Takano, S.; Otaki, S.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1985, 485.
21. (b) Angell, R.; Parsons, P. J.; Naylor, A.; Tyrrell, E. Synlett 1992, 599.
22. Cookson, R. C.; Gilani, S. S. H.; Stevens, I. D. R. Tetrahedron Lett. 1962, 3, 615.
23. Baum, S. M.; Trabanco, A.-A.; Garrido Montalban, A.; Micallef, A. S.; Zhong, C.; Meunier, H. G.; Suhling, K.; Phillips, D.; White, A. J. P.; Williams, D. J.; Barrett, A. G. M.; Hoffman, B. M. J. Org. Chem. 2003, 68, in press.
24. 13C NMR, and LRMS were obtained, due to instabilities of the products.