A synthesis of 17-epi-calcidiol

Tetrahedron Letters

Volumn 45, Issue 40, 2004, Pages 7479-7482

  Kurek Tyrlik, Alicja ^a   Michalak, Karol ^a   Urbanczyk Lipkowska, Zofia ^a   Wicha, Jerzy ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

Alkyl diazoacetates; Cyclopropanation; Lithium in liquid ammonia; Vitamin D synthesis

Indexed keywords

17 EPICALCIDIOL; ACETIC ACID DERIVATIVE; ALKYL GROUP; AMMONIA; ANDROSTANE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; COLECALCIFEROL DERIVATIVE; CYCLOPROPANE DERIVATIVE; ESTER DERIVATIVE; LITHIUM; PALLADIUM COMPLEX; PREGNANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CRYSTAL STRUCTURE; DERIVATIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ESTERIFICATION; LIQUID; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 4444364960     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.08.050     Document Type: Article

References (22)

1. For leading references, see: R. Bouillon, W.H. Okamura, and A.W. Norman Endoc. Rev. 16 1995 200 257
2. 3 and its medicinal uses G.P. Ellis D.K. Luscombe A.W. Oxford Progr. Med. Chem. Vol. 35 1998 Elsevier Amesterdam 1 56
3. For a recent review, see: G.H. Posner, and M. Kahraman Eur. J. Org. Chem. 2003 3889 3895
4. G.H. Posner, and M. Kahraman Eur. J. Org. Chem. 2003 4937 4937
5. Recent works include: F. Sussman, A. Rumbo, M.C. Villaverde, and A. Mourino J. Med. Chem. 47 2004 1613 1616
6. Y.J. Chen, L.J. Gao, I. Murad, A. Verstuyf, L. Verlinden, C. Verboven, R. Bouillon, D. Viterbo, M. Milanesio, D. Van Haver, M. Vandewalle, and P.J. De Clercq Org. Biomol. Chem. 1 2003 257 267
7. Y. Fall, O. Diouf, G. Gomez, and T. Bolano Tetrahedron Lett. 44 2003 6069 6072
8. S. Marczak, A. Przezdziecka, J. Wicha, A. Steinmeyer, and U. Zuegel Bioorg. Med. Chem. Lett. 11 2001 63 66
9. 3 and Related Stereoisomers. In Vitamin D Endocrine System. Proceedings of the 11th Workshop on Vitamin D; Norman, A. W.; Bouillon, R.; Thomasset, M., Eds.; University of California, Riverside (Calif.), 2000; pp 81-84
10. A. Przezdziecka, A. Kurek-Tyrlik, and J. Wicha Collect. Czech. Chem. Commun. 67 2002 1658 1668
11. A.J. Anciaux, A.J. Hubert, A.F. Noels, N. Petiniot, and P. Teyssie J. Org. Chem. 45 1980 695 702
12. M.W. Majchrzak, A. Kotełko, and J.B. Lombert Synthesis 1983 469 470
13. M.P. Doyle Chem. Rev. 86 1986 919 939
14. H.O. House, and C.J. Blankley J. Org. Chem. 33 1968 47 53
15. For a review, see: S. von Angerer Cyclopropanes: Transformations, Ring-opening Reactionsâ€"by Reductive Fission A. de Meijere Carbocyclic Three-Membered Ring Compounds Vol. E17c 1996 Georg Thieme Stuttgart 2045 2053
16. For recent work, see: A. Srikrishna, and S.S.V. Ramasastry Tetrahedron Lett. 45 2004 379 382
17. With ester 5a cleavage of the C-O bond (path b) is preferred over cleavage of the C-C bond (path a), presumably due to the stability of the tert-butyl radical.
18. J.R. Parikh, and W.v.E. Doering J. Am. Chem. Soc. 89 1967 5505 5507
19. J. Wicha, and K. Bal J. Chem. Soc., Perkin Trans. 1 1978 1282 1288
20. Crystallographic data (excluding structure factors) for the structure in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 242072. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge BC2 1EZ, UK [fax. +44-(0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk ]
21. J.J. Partridge, S. Faber, and M. Uskokovic Helv. Chim. Acta 57 1974 764 770
22. For an example, see: DeLuca, H. F.; Wicha, J. Method of Treating Hypoparathroidism with 20(S) Vitamin D Compounds. U.S. Patent 5,552,392; Appl. November 3 1993, 1996