An efficient stereoselective synthesis of 1α,24(R)-dihydroxyvitamin D3 by the dienyne route

Tetrahedron

Volumn 53, Issue 13, 1997, Pages 4703-4714

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

^a CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

COLECALCIFEROL DERIVATIVE; TACALCITOL;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030892390     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00139-7     Document Type: Article

References (36)

1. For an excellent review, see: Bouillon, R.; Okamura, W. H.; Norman, A. W. Structure-Function Relationships in the Vitamin D Endocrine System. Endocr. Rev. 1995, 16, 200-257.
2. Compound 2. (a) Perlman, K. L.; Sicinski, R. R.; Schnoes, H. K.; DeLuca, H. F. Tetrahedron Lett. 1990, 31, 1823.
3. (b) Bouillon, R.; Sarandeses, L. A.; Allewaert, K.; Zhao, J.; Mascareñas, J. L.; Mouriño, A.; Vrielynck, S.; De Clercq, P.; Vandewalle, M. J. Bone Min. Res. 1993, 8, 1009. Compound 3.
4. (c) Uskokovic, M. R.; Baggiolini, E.; Shiuey, S. J.; Hennessy, B; Kiegiel, J.; Daniewski, A. R.; Pizzolato, G.; Coustney, L. F.; Horst, R. L. Gene Regulation, Structure-Function Analysis and Clinical Application. Norman, A. W.; Bouillon, R.; Thomasset, M. (Eds.) Walter de Gruyter, Berlin 1991, pp 139-145. Compound 4.
5. (d) Bouillon, R.; Allewaert, K.; Vanleeuwen 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.; Birkenhager, J.C. J. Biol. Chem. 1992, 267, 3044. Compound 5a.
6. (e) Binderup, L.; Latini, S.; Binderup, E.; Bretting, C.; Calverley, M.; Hansen, K. Biochem. Pharmacol. 1991, 42, 1569. Compound 5b.
7. (f) Abe, J.; Morikawa, M.; Miyamoto, K.; Kaiho, S.; Fukushima, M.; Miyaura, C.; Abe, E.; Suda, T.; Nishii, Y. FEBS Lett. 1987, 226, 58. Compound 5c.
8. (g) Perlman, K.; Kutner, A.; Prahl, J.; Smith, C.; Inaba, M.; Schnoes, H. K.; DeLuca, H. F. Biochemistry 1990, 29, 190. Compound 5d.
9. (h) Calverley, M. J. Tetrahedron 1987, 43, 4609.
10. (i) Binderup, L.; Kragballe, K. Rev. Contemp. Pharmacother. 1992, 3, 357. Compound 5e.
11. (j) Okamoto, M.; Fujii, T.; Tanaka, T. Tetrahedron 1995, 51, 5543 and references therein.
12. (a) Morisaki, M.; Koizumi, N.; Ikekawa, N.; Takeshita, T. J. Chem. Soc., Perkin. Trans. I 1975, 1421.
13. (b) Koch, P.; Nakatani, Y.; Luu, B.; Ourisson, G. Bull. Soc. Chim. Fr. 1983, 189.
14. (c) Okamoto, M.; Tabe, M; Fujii, T.; Tanaka, T. Tetrahedron Asymmetry 1995, 6, 767.
15. Trost, B. M.; Dumas.; J.; Villa.; M. J. Am. Chem. Soc. 1992, 114, 9836.
16. Dixon, J.; Littlewood, P. S.; Lythgoe, B.; Saksena, A. K. J. Chem. Soc., Chem. Commun. 1970, 993.
17. (a) Castedo, L.; Mouriño, A.; Sarandeses, L. A. Tetrahedron Lett. 1986, 27, 1523.
18. (b) Castedo, L.; Mascareñas, J. L.; Mouriño, A.; Sarandeses, L. A. Tetrahedron Lett. 1988, 29, 1203.
19. (c) Castedo, L.; Mascareñas, J. L.; Sarandeses, L. A. Tetrahedron 1991, 47, 3485.
20. (d) Pérez-Sestelo, J.; Mascareñas, J.L.; Castedo, L.; Mouriño, A. J. Org. Chem. 1993, 58, 118.
21. For excellent discussions on various synthetic approaches to vitamin D metabolites and their analogues, see: (a) Dai, H.; Posner, G. H. Synthesis 1994, 1383-1398.
22. (b) Zhu, G.-D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877-1952.
23. 2: Sardina; F. J.; Mouriño, A.; Castedo. L. J. Org. Chem. 1986, 51, 1264.
24. Leyes, G.A.; Okamura, W. H. J. Am. Chem. Soc. 1982, 104, 6099.
25. Wovkulich, P. M.; Barcelos, F.; Batcho, A. D.; Sereno, J. F.; Baggiolini, E. G.; Hennessy, B. M.; Uskokovic, M. R. Tetrahedron 1984, 40, 2283.
26. Kocienski, P. J. Protecting Groups. Georg Thieme Verlag. Stuttgart-New York, 1994.
27. Fall, Y.; Torneiro, M.; Castedo, L.; Mouriño, A. Tetrahedron Lett. 1992, 33, 6683.
28. Cuvigny, T.; Larcheveque, M.; Normant, H. Bull. Soc. Chim. Fr. 1973, 1174.
29. Linderman, R. J.; Jaber, M.; Griedel, B. D. J. Org. Chem. 1994, 59, 6499.
30. (a) Hendrickson, J. B.; Bergeron, R. Tetrahedron Lett. 1973, 14, 4607.
31. (b) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1983, 24, 979.
32. The efficient preparation of this compound by Okamura and coworkers makes the enyne route particularly attractive for the preparation of vitamin D analogues: (a) Okamura, W. H.; Aurrecoechea, J. M.; Gibbs, R. A.; Norman, A. W. J. Org. Chem. 1989, 54, 4072.
33. For previous syntheses of enyne 8, see: (b) Baggiolini, E. G.; Hennessy, B. M.; Iacobelli, J. A.; Uskokovic, M. R.; Tetrahedron Lett. 1987, 28, 2095, and
34. (c) Castedo, L.; Mascareñas, J. L.; Mouriño, A. Tetrahedron Lett. 1987, 28, 2099.
35. Torneiro, M.; Fall, Y.; Castedo, L.; Mouriño, A. Tetrahedron Lett. 1992, 33, 105.
36. Still, W. C.; Kahu, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.