Efficient and versatile synthesis of A-ring precursors of 1α,25-dihydroxyvitamin D3 and analogues. Application to the synthesis of Lythgoe-Roche phosphine oxide

Tetrahedron Letters

Volumn 38, Issue 26, 1997, Pages 4713-4716

  Mouriño, Antonio ^a   Torneiro, Mercedes ^a   Vitale, Cristian ^a   Fernández, Sara ^a   Pérez Sestelo, José ^a   Anné, Sofia ^a   Gregorio, Carlos ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CALCITRIOL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030913417     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01005-8     Document Type: Article

References (32)

1. (a) Vitamin D, The Calcium Homeostatic Steroid Hormone; Norman, A. W., Ed.; Academic Press: New York, 1979.
2. 3. In Comprehensive Medicinal Chemistry; Hansch, C., Sammes, P. C.; Taylor, J. B., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, 1129-1143.
3. a) Uskokovic', M. R. Recent Advances in Vitamin D Chemistry and Pharmacological Activity. Bioorg. Med. Chem. Lett. 1993, 3, 1783-1896.
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. (a) Calverley, M. J.; Jones, G. "Vitamin D" in Antitumor Steroids; Blickenstaff, R. T., Ed.; Academic Press: San Diego, 1992; 193-27.
6. (b) Bouillon, R.; Okamura, W. H.; Norman, A. W. Structure-Function Relationships in the Vitamin D Endocrine System. Endocr. Rev. 1995, 16, 200-257 and references therein.
7. a) Dai, H.; Posner, G. H. Synthetic Approaches to Vitamin D. Synthesis 1994, 1383-1398.
8. (b) Zhu, G-D.; Okamura, W. H. Synthesis of Vitamin D (Calciferol). Chem. Rev. 1995, 95, 1877-1952.
9. (a) Kocienski, P. J.; Lythgoe, B. J. Chem. Soc., Perkin Trans. I 1980, 1440.
10. (b) Lythgoe, B. Chem. Soc. Rev. 1981, 449.
11. (c) Baggiolini, E. G.; Iacobelli, J. A.; Hennessy, B. M.; Batcho, A. D.; Sereno, J. F.; Uskokovic', M. R. J. Org. Chem. 1986, 51, 3098.
12. (a) Baggiolini, E. G.; Iacobelli, J. A.; Hennessy, B. M.; Uskokovic', M. R. J. Am. Chem. Soc. 1982, 104, 2945.
13. (b) Hatakeyama, S.; Numata, H.; Osanai, K.; Takano, S. J. Org. Chem. 1989, 54, 3515.
14. (c) Kobayashi, S.; Shibata, J.; Shimada, M.; Ohno, M. Tetrahedron Lett. 1990, 31, 1577.
15. (d) Posner, G. H.; Kinter, C. M. J. Org. Chem. 1990, 55, 3967.
16. (e) Posner, G. H.; Carry, J.-C.; Anjeh, T. E. N.; French, A. N. J. Org. Chem. 1992, 57, 7012.
17. (f) Stork, G.; Hutchinson, D.; Okabe, M.; Parker, D.; Ra, C.; Ribéreau, F.; Suzuki, T.; Zebovitz, T. Pure & Appl. Chem. 1992, 64, 1809.
18. (g) Kabat, M. M.; Lange, M.; Wovkulich, P. M.; Uskokovic', M. R. Tetrahedron Lett. 1992, 33, 7701.
19. (h) De Schrijver, J.; De Clerq, P.J. Tetrahedron Lett. 1993, 34, 4369.
20. (i) Nagasawa, K.; Ishihara, H.; Zako, Y., Shimizu, I. J. Org, Chem. 1993, 58, 2523.
21. (j) Chen, C.; Crich, D. Tetrahedron 1993, 49, 7943.
22. (k) Torneiro, M.; Vrielynck, S.; García, A. M.; Mascareñas, J. L.; Castedo, L.; Mouriño, A. In Vitamin D, A . Pluripotent Steroid Hormone: Structural Studies, Molecular Endocrinology and Clinical Applications; Norman, A. W., Bouillon, R., Thomasset, M., Eds.; Walter de Gruyter: Berlin 1994, 39.
23. (l) Tazumi. K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1994, 1903.
24. (m) Hatakeyama, S.; Irie, H.; Shintani, T.; Noguchi, Y.; Yamada, H.; Nishizawa, M. Tetrahedron 1994, 50, 13369.
25. (n) Vrielynck, S.; Vandewalle, M.; Garcia, A.; Mascareñas, J. L.; Mouriño, A. Tetrahedron Lett. 1995, 36, 9023.
26. Palladium-catalysed cyclization-carbonylation has been successfully carried out on simpler substrates such as vinylic bromides lacking a hydroxyl group at C-1 (steroidal numbering), See: Nuss, J. M.; Murphy, M. M.; Rennels, R. A.; Heravi, M. H.; Mohr, B. J. Tetrahedron Lett. 1993, 34, 3079.
27. Mascareñas, J. L.; Sarandeses, L. A.; Castedo, L.; Mouriño, A. Tetrahedron 1991, 47, 3485.
28. Klein, E.; Ohloff, G. Tetrahedron 1963, 19, 1091.
29. Ohloff, G.; Paulak, M. Helv. Chim. Acta. 1973, 56, 1176.
30. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1992, 3769.
31. 13C NMR.
32. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299.