Copper-mediated alkylation of vitamin DC-ring. Synthesis of C11-functionalized 1α,25-dihydroxyvitamin D3

Tetrahedron

Volumn 53, Issue 31, 1997, Pages 10851-10870

  Torneiro, Mercedes ^a   Fall, Yagamare ^a   Castedo, Luis ^a   Mouriño, Antonio ^a  

^a CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CALCITRIOL; CALCITRIOL DERIVATIVE;

AFFINITY CHROMATOGRAPHY; ALKYLATION; ARTICLE; DRUG PURIFICATION; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030753044     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00692-3     Document Type: Article

References (61)

1. This work was taken in part from the doctoral thesis of Mercedes Torneiro (University of Santiago de Compostela, January 1994). Part of it has been described in a preliminary communication: Torneiro, M.; Fall, Y.; Castedo, L.; Mouriño, A.; Tetrahedron Lett. 1992, 33, 105.
2. Norman, A. W., Ed. Vitamin D, The Calcium Homeostatic Steroid Hormone. Academic Press: New York, 1979.
3. (a) Uskokovic', M. R. Recent Advances in Vitamin D Chemistry and Pharmacological Activity; Bioorg. Med. Chem. Lett. 1993, 3, 1783.
4. (b) Norman, A. W.; Bouillon, R.; Thomasset, M.; Eds. Vitamin D, A Pluripotent Steroid Hormone: Structural Studies, Molecular Endocrinology and Clinical Applications. Walter de Gruyter: Berlin, 1994.
5. For a review on Vitamin D analogues see: Bouillon, R.; Okamura, W. H.; Norman, A. W. Structure-Function Relationships in the Vitamin D Endocrine System; Endocr. Rev. 1995, 200.
6. 3 has also been observed, both at cellular and subcellular levels. (a) Baran, D. T. J. Cell. Biochem. 1994, 56, 303.
7. (b) Boyan, B. D.; Dean, D. D.; Sylvia, V. L.; Schwartz, Z. J. Cell. Biochem. 1994, 56, 331.
8. (c) Beno, D. W. A.; Brady, L. M.; Bissonnette, M.; Davis, B. H. J. Biol. Chem. 1995, 270, 3542.
9. Bissonnette, M.; Wali, R. K.; Hartmann, S. C.; Niedziela, S. M.; Roy, H. K.; Tien, X.-Y.; Sitrin, M. D.; Brasitus, T. A. J. Clin. Invest. 1995, 95, 2215.
10. (a) Baker, A. R.; McDonnell, D. P.; Hughes, M.; Crisp, T. M.; Mangelsdorf, D. J.; Haussler, M. R.; Pike, J. W.; Shine, J.; O'Malley, B. W. Proc. Natl. Acad. Sci. USA 1988, 85, 3294.
11. (b) Lowe, K. E.; Maiyar, A. C.; Norman, A. W. "Vitamin D Mediated Gene Expression;" Crit. Rev. Eukar. Gene Exp. 1992, 2, 65.
12. Towers, T. L.; Luisi, B. F.; Asianov, A.; Freedman, L. P. Proc. Natl. Acad. Sci. USA 1993, 90, 6310.
13. (a) Allan, G. F.; Leng, X.; Tsai, S. Y.; Weigel, N. L.; Edwards, D. P.; Tsai, M.-J.; O'Malley, B. W. J. Biol. Chem. 1992, 267, 19513.
14. (b) Peleg, S.; Sastry, M.; Collins, E. D.; Bishop, J. E.; Norman, A. W. J. Biol. Chem. 1995, 270, 10551.
15. (a) Some empirical information can be gained from structure-activity relationships of vitamin D analogues: See reference 4.
16. (b) It has been suggested that the 1α- and 25-hydroxy groups, necessary for the hormone analogues to keep biological activity, may participate in the formation of hydrogen bonds to the receptor: Allegreto, E. A.; Pike, J. W.; Haussler, M. R. Biochem. Biophys. Res. Comm. 1987, 147, 479.
17. Parikh, I.; Cuatrecasas, P. Chem. Eng. News 1985, 63, 17.
18. (a) Bouillon, R.; De Clercq, P. J.; Eliard, P.; Vandewalle, M. Eur. Pat. 341,158 (Chem. Abs. 1990, 112, 198894s).
19. (b) Zhu, G.-D.; Van Haver, D.; Jurriaans, H.; De Clercq, P. J. Tetrahedron 1994, 50, 7049.
20. 3 and their 11-substituted analogues, see: (c) Pumar, C.; Aurrecoechea, J. M.; Gibbs, R. A.; Norman, A. W.; Okamura, W. H. Vitamin D: Molecular, Cellular and Clinical Endocrinology. Walter de Gruyter: Berlin, 1988, 54.
21. (d) Okamura, W. H.; Aurrecoechea, J. M.; Gibbs, R. A.; Norman, A. W. J. Org. Chem. 1989, 54, 4072.
22. Bouillon, R.; Allewaert, K.; Van Leeuwen, J. P. T. M.; Tan, B.-K.; Xiang, D. Z.; De Clercq, P.; Vandewalle, M.; Pols, H. A. P.; Bos, M. P.; Van Baelen, H.; Birkenhäger, J. C. J. Biol. Chem. 1992, 267, 3044.
23. (a) Lythgoe, B.; Moran, T. A.; Nambudiry, M. E.; Tideswell, J. T.; Wright, P. W. J. Chem. Soc., Perkin Trans, I. 1978, 590.
24. (b) Kocienski, P. J.; Lythgoe, B.; Waterhouse, I. J. Chem. Soc., Perkin Trans. I 1980, 1045.
25. (c) Baggiolini, F. G.; Iacobelli, J. A.; Hennessy, B. M.; Batcho, A. D.; Sereno, J. F.; Uskokovic', M.R. J. Org. Chem. 1986, 51, 3098.
26. The dienyne approach was first developed by Lythgoe and co-workers and later improved by our group: (a) Dixon, J.; Littlewood, P. S.; Lythgoe, B.; Saksena, A. K. J. Chem. Soc., Chem. Commun. 1970, 993.
27. (b) Castedo, L.; Mouriño, A.; Sarandeses, L. A. Tetrahedron Lett. 1986, 27, 1523.
28. (c) Castedo, L.; Mascareñas, J. L.; Mouriño, A.; Sarandeses, L. A. Terahedron Lett. 1988, 29, 1203.
29. (d) Mascareñas, J. L.; Sarandeses, L. A.; Castedo, L.; Mouriño, A. Tetrahedron 1991, 47, 3485.
30. (a) Okamura, W. H.; Aurrecochea, J. M.; Gibbs, R. A.; Norman, A. W. J. Org. Chem. 1989, 54, 4072.
31. (b) Enas, J. D.; Palenzuela, J. A.; Okamura, W. H. J. Am. Chem. Soc. 1991, 113, 1355.
32. (a) Corey, E. J.; Boaz, N.W. Tetrahedron Lett. 1985, 26, 6015.
33. (b) Corey, E. J.; Boaz, N. Tetrahedron Lett. 1985, 26, 6019.
34. (c) Horiguchi, Y.; Matsuzawa, S.; Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1986, 34, 4025.
35. (d) Nakamura, E.; Matsuzawa, S.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1986, 34, 4029.
36. Cacchi, S.; Morera, E.; Ortar, G. Tetrahedron Lett. 1984, 25, 4821.
37. (a) Scott, W. J.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630.
38. (b) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033.
39. Inhoffen, H. H.; Quinkert, G.; Schütz, S.; Kampe, D.; Domagk, G. F. Chem. Ber. 1957, 90, 664.
40. Goering, H. L.; Seitz, Jr., E. P.; Tseng, C. C. J. Org. Chem. 1981, 46, 5304.
41. (a) Gallina, C.; Ciattini, P. G. J. Am. Chem. Soc. 1979, 101, 1035.
42. (b) Goering, H. L.; Kantner, S. S.; Tseng, C. C. J. Org. Chem. 1983, 48, 715.
43. Compound 13 had NMR spectra different to 9.
44. For cuprate-mediated alkylation of semi-rigid allylic esters, see: (a) Goering, H. L.; Kantner, S. S. J. Org. Chem. 1984, 49, 422.
45. (b) Goering, H. L.; Kantner, S. S.; Seitz, Jr. E. P. J. Org. Chem. 1985, 50, 5495.
46. (c) Bäckwall, J.-E.; Andersson, P. G.; Stone, G. B.; Gogoll, A. J. Org. Chem. 1991, 56, 2988.
47. (a) Tseng, C. C.; Paisley, S. D.; Goering, H. L. J. Org. Chem. 1986, 51, 2884.
48. (b) Tseng, C. C.; Yen, S.-J.; Goering, H. L. ibid. 1986, 51, 2892 and references therein.
49. For a review on the synthesis of vitamin D metabolites and analogues see: Zhu, G.-D; Okamura, W. H. Synthesis of Vitamin D (Calciferol); Chem. Rev. 1995, 95, 1877.
50. Sardina, J. F.; Mouriño, A.; Castedo, L. J. Org. Chem. 1986, 51, 1264.
51. (a) Hesse, R. H. EP 78,704 (Chem. Abs. 1983, 99, 176164q).
52. (b) Andrews, D. R.; Barton, D. H. R.; Hesse, R. H.; Pechet, M. M. J. Org. Chem. 1986., 51, 4819; and ref. therein.
53. Cuvigny, T.; Larcheveque, M.; Normant, H. Bull. Soc. Chim. Fr. 1973, 1174.
54. (a) Fall, Y.; Torneiro, M; Castedo, L.; Mouriño, A. Tetrahedron Lett. 1992, 33, 6683.
55. (b) Fall, Y.; Torneiro, M; Castedo, L.; Mouriño, A. Tetrahedron 1997, 53, 4703.
56. Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011.
57. Büchi, G.; Wüest, H. J. Org. Chem. 1969, 34, 1122.
58. (a) Baggiolini, E. G.; Hennessy, B. M.; Iacobelli, J. M.; Uskokovic, M. R. Tetrahedron Lett. 1987, 28, 2095.
59. (b) Castedo, L.; Mascareñas, J. L.; Mouriño, A. Tetrahedron Lett. 1987, 28, 2099.
60. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
61. Meyers, A. I.; Slade, J.; Smith, R. K.; Mihelich, E. P.; Hershenson, F. M.; Liang, C. D.; J. Org. Chem. 1979, 44, 2247.