Asymmetric Synthesis of Vitamin D3 Analogues: Organocatalytic Desymmetrization Approach toward the A-Ring Precursor of Calcifediol

Organic Letters

Volumn 17, Issue 21, 2015, Pages 5452-5455

  Wang, Haifeng ^a   Yan, Linjie ^a   Wu, Yan ^a   Lu, Yipei ^a   Chen, Fener ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; ALLYL ALCOHOL; CALCIFEDIOL; COLECALCIFEROL; PROPANOL; UREA;

ANALOGS AND DERIVATIVES; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANHYDRIDES; CALCIFEDIOL; CATALYSIS; CHOLECALCIFEROL; MOLECULAR STRUCTURE; PROPANOLS; STEREOISOMERISM; UREA;

EID: 84946811405     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b02813     Document Type: Article

References (29)

1. Feldman, D., Glorieux, F. H., Pike, J. W., Eds. Vitamin D; Academic Press: San Diego, CA, 1997.
2. Feldman, D., Pike, J. W., Glorieux, F. H., Eds. Vitamin D, 2 nd ed.; Elsevier Academic Press: New York, 2005.
3. Bouillon, R.; Okamura, W. H.; Norman, A. W. Endocr. Rev. 1995, 16, 200-257 10.1210/edrv-16-2-200
4. Campbell, M. J.; Adorini, L. Expert Opin. Ther. Targets 2006, 10, 735-748 10.1517/14728222.10.5.735
5. Jones, G. Annu. Rev. Nutr. 2013, 33, 23-44 10.1146/annurev-nutr-071812-161203
6. Fraser, D. R.; Kodicek, E. Nature 1970, 228, 764-766 10.1038/228764a0
7. Cheng, J. B.; Levine, M. A.; Bell, N. H.; Mangelsdorf, D. J.; Russell, D. W. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 7711-7715 10.1073/pnas.0402490101
8. Jones, G.; Strugnell, S. A.; DeLuca, H. F. Physiol. Rev. 1998, 78, 1193-1231
9. Holick, M. F. Mayo Clin. Proc. 2006, 81, 353-373 10.4065/81.3.353
10. Zhu, G. D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877-1952 10.1021/cr00038a007
11. Dai, H.; Posner, G. H. Synthesis 1994, 1994, 1383-1398 10.1055/s-1994-25697
12. Frosch, J. V.; Harrison, I. T.; Lythgoe, B.; Saksena, A. K. J. Chem. Soc., Perkin Trans. 1 1974, 2005-2009 10.1039/p19740002005
13. Toh, H. T.; Okamura, W. H. J. Org. Chem. 1983, 48, 1414-1417 10.1021/jo00157a004
14. Lythgoe, B.; Milner, J. R.; Tideswell, J. Tetrahedron Lett. 1975, 16, 2593-2596 10.1016/S0040-4039(00)75187-2
15. Lythgoe, B.; Nambudiry, M. E. N.; Tideswell, J. Tetrahedron Lett. 1977, 18, 3685-3688 10.1016/S0040-4039(01)83327-X
16. Lythgoe, B.; Manwaring, R.; Milner, J. R.; Moran, T. A.; Nambudiry, M. E. N.; Tideswell, J. J. Chem. Soc., Perkin Trans. 1 1978, 387-395 10.1039/p19780000387
17. Miles, W. H.; Connell, K. B.; Ulas, G.; Tuson, H. H.; Dethoff, E. A.; Mehta, V.; Thrall, A. J. J. Org. Chem. 2010, 75, 6820-6829 10.1021/jo101155c
18. Chen, F. E.; Wang, S. X. CN Patent 101362100A, Feb 11, 2009.
19. Yang, H. J.; Xiong, F. J.; Li, J.; Chen, F. E. Chin. Chem. Lett. 2013, 24, 553-558 10.1016/j.cclet.2013.04.009
20. Yang, H. J.; Xiong, F. J.; Chen, X. F.; Chen, F. E. Eur. J. Org. Chem. 2013, 2013, 4495-4498 10.1002/ejoc.201300464
21. Van Tamelen, E. E.; Shamma, M. J. Am. Chem. Soc. 1954, 76, 2315-2317 10.1021/ja01638a010
22. Goldsmith, D. J.; John, T. K.; Van Middlesworth, F. Synth. Commun. 1980, 10, 551-557 10.1080/00397918008069332
23. CCDC 1426870 contains the crystallographic data for 5. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/datarequest/cif.
24. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901-3924 10.1016/S0040-4020(01)97173-X
25. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron Lett. 1983, 24, 4979-4982 10.1016/S0040-4039(01)99826-0
26. Sebahar, P. R.; Williams, R. M. J. Am. Chem. Soc. 2000, 122, 5666-5667 10.1021/ja001133n
27. Posner, G. H.; Kinter, C. M. J. Org. Chem. 1990, 55, 3967-3969 10.1021/jo00300a001
28. Posner, G. H.; Crouch, R. D.; Kinter, C. M.; Carry, J. C. J. Org. Chem. 1991, 56, 6981-6987 10.1021/jo00025a008
29. Posner, G. H.; Nelson, T. D.; Guyton, K. Z.; Kensler, T. W. J. Med. Chem. 1992, 35, 3280-3287 10.1021/jm00095a026