An efficient solid-phase synthesis of the vitamin D3 system [2]

Journal of the American Chemical Society

Volumn 121, Issue 28, 1999, Pages 6749-6750

  Doi, Takayuki ^a   Hijikuro, Ichiro ^a   Takahashi, Takashi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CALCITRIOL; VITAMIN D;

ALKYLATION; CHEMICAL MODIFICATION; DRUG STRUCTURE; HORMONE ACTION; LETTER; REACTION ANALYSIS; STRUCTURE ANALYSIS; VITAMIN METABOLISM;

EID: 0033591904     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990739c     Document Type: Letter

References (30)

1. Norman, A. W., Bouillon, R., Thomasset, M., Eds.; Vitamin D: Gene Regulation, Structure Function Analysis and Clinical Application; Walter de Gruyter and Co.: Berlin; 1991.
2. Bouillon, R.; Okamura, W. H.; Norman, A. W. Endocr. Rev. 1995, 16, 200.
3. Zhu, G.-D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877. For recent reports of the preparation of the A-ring moieties, see: Sicinski, R. R.; Prahl, J. M.; Smith, C. M.; DeLuca, H. F. J. Med. Chem. 1998, 41, 4662. Posner, G. H.; Lee, J. K.; White, M. C.; Hutchings, R. H.; Dai, H.; Kachinski, J. L.; Dolan, P.; Kensler, T. W. J. Org. Chem. 1997, 62, 3299. Hatakeyama, S.; Ikeda, T. Maeyama, J. Esumi, T.; Iwabuchi, Y.; Irie, H.; Kawase, A.; Kubodera, N. Bioorg. Med. Chem. Lett. 1997, 7, 2871.
4. Zhu, G.-D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877. For recent reports of the preparation of the A-ring moieties, see: Sicinski, R. R.; Prahl, J. M.; Smith, C. M.; DeLuca, H. F. J. Med. Chem. 1998, 41, 4662. Posner, G. H.; Lee, J. K.; White, M. C.; Hutchings, R. H.; Dai, H.; Kachinski, J. L.; Dolan, P.; Kensler, T. W. J. Org. Chem. 1997, 62, 3299. Hatakeyama, S.; Ikeda, T. Maeyama, J. Esumi, T.; Iwabuchi, Y.; Irie, H.; Kawase, A.; Kubodera, N. Bioorg. Med. Chem. Lett. 1997, 7, 2871.
5. Zhu, G.-D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877. For recent reports of the preparation of the A-ring moieties, see: Sicinski, R. R.; Prahl, J. M.; Smith, C. M.; DeLuca, H. F. J. Med. Chem. 1998, 41, 4662. Posner, G. H.; Lee, J. K.; White, M. C.; Hutchings, R. H.; Dai, H.; Kachinski, J. L.; Dolan, P.; Kensler, T. W. J. Org. Chem. 1997, 62, 3299. Hatakeyama, S.; Ikeda, T. Maeyama, J. Esumi, T.; Iwabuchi, Y.; Irie, H.; Kawase, A.; Kubodera, N. Bioorg. Med. Chem. Lett. 1997, 7, 2871.
6. Zhu, G.-D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877. For recent reports of the preparation of the A-ring moieties, see: Sicinski, R. R.; Prahl, J. M.; Smith, C. M.; DeLuca, H. F. J. Med. Chem. 1998, 41, 4662. Posner, G. H.; Lee, J. K.; White, M. C.; Hutchings, R. H.; Dai, H.; Kachinski, J. L.; Dolan, P.; Kensler, T. W. J. Org. Chem. 1997, 62, 3299. Hatakeyama, S.; Ikeda, T. Maeyama, J. Esumi, T.; Iwabuchi, Y.; Irie, H.; Kawase, A.; Kubodera, N. Bioorg. Med. Chem. Lett. 1997, 7, 2871.
7. For a review, see: Fruchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17.
8. 3, see: 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; Torneiro, M.; Fall, Y.; Castedo, L.; Mourino, A. Tetrahedron Lett. 1992, 33, 105; Zhu, G.-D., Van Haver, D.; Jurriaans, H.; De Clercq, P. J. Tetrahedron 1994, 50, 7049.
9. 3, see: 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; Torneiro, M.; Fall, Y.; Castedo, L.; Mourino, A. Tetrahedron Lett. 1992, 33, 105; Zhu, G.-D., Van Haver, D.; Jurriaans, H.; De Clercq, P. J. Tetrahedron 1994, 50, 7049.
10. 3, see: 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; Torneiro, M.; Fall, Y.; Castedo, L.; Mourino, A. Tetrahedron Lett. 1992, 33, 105; Zhu, G.-D., Van Haver, D.; Jurriaans, H.; De Clercq, P. J. Tetrahedron 1994, 50, 7049.
11. 3, see: 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; Torneiro, M.; Fall, Y.; Castedo, L.; Mourino, A. Tetrahedron Lett. 1992, 33, 105; Zhu, G.-D., Van Haver, D.; Jurriaans, H.; De Clercq, P. J. Tetrahedron 1994, 50, 7049.
12. Lythgoe, B.; Moran, T. A.; Nambudiry, M. E. N.; Tideswell, J.; Wright, P. W. J. Chem. Soc., Perkin Trans. I 1978, 590.
13. Toh, H. T.; Okamura, W. H. J. Org. Chem. 1983, 48, 1414.
14. Baggiolini, E. G.; Iacobelli, J. A.; Hennessy, B. M.; Batcho, A. D.; Sereno, J. F.; Uskokovic, M. R. J. Org. Chem. 1986, 51, 3098.
15. 3 system; see: Andrews, D. R.; Barton, D. H. R.; Hesse, R. H.; Pechet, M. M. J. Org. Chem. 1986, 51, 4819.
16. Okano, T.; Tsugawa, N.; Masuda, S.; Takeuchi, A.; Kobayashi, T.; Takita, Y.; Nishii, Y. Biochem. Biophys. Res. Commun. 1989, 163, 1444; Tobayashi, T.; Okano, T.; Tsugawa, N.; Murano, M.; Masuda, S.; Takeuchi, A., Sato, K.; Nishii, Y. Bioorg. Med. Chem. Lett. 1993, 3, 1815; Tsurukami, H.; Nakamura, T.; Suzuki, K.; Sato, K.; Higuchi, Y.; Nishii, Y. Calcif. Tissue. Int. 1994, 54, 142.
17. Okano, T.; Tsugawa, N.; Masuda, S.; Takeuchi, A.; Kobayashi, T.; Takita, Y.; Nishii, Y. Biochem. Biophys. Res. Commun. 1989, 163, 1444; Tobayashi, T.; Okano, T.; Tsugawa, N.; Murano, M.; Masuda, S.; Takeuchi, A., Sato, K.; Nishii, Y. Bioorg. Med. Chem. Lett. 1993, 3, 1815; Tsurukami, H.; Nakamura, T.; Suzuki, K.; Sato, K.; Higuchi, Y.; Nishii, Y. Calcif. Tissue. Int. 1994, 54, 142.
18. Okano, T.; Tsugawa, N.; Masuda, S.; Takeuchi, A.; Kobayashi, T.; Takita, Y.; Nishii, Y. Biochem. Biophys. Res. Commun. 1989, 163, 1444; Tobayashi, T.; Okano, T.; Tsugawa, N.; Murano, M.; Masuda, S.; Takeuchi, A., Sato, K.; Nishii, Y. Bioorg. Med. Chem. Lett. 1993, 3, 1815; Tsurukami, H.; Nakamura, T.; Suzuki, K.; Sato, K.; Higuchi, Y.; Nishii, Y. Calcif. Tissue. Int. 1994, 54, 142.
19. Takahashi, T.; Nakazawa, M. Synlett 1993, 37; Takahashi, T.; Nakazawa, M.; Sakamoto, Y.; Houk, K. N. Tetrahedron Lett. 1993, 34, 4075.
20. Takahashi, T.; Nakazawa, M. Synlett 1993, 37; Takahashi, T.; Nakazawa, M.; Sakamoto, Y.; Houk, K. N. Tetrahedron Lett. 1993, 34, 4075.
21. Brooks, D. W.; Lu, L. D.-L.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1979, 18, 72.
22. 6.
23. Yokoyama, H.; Takahashi, T. Synlett 1997, 187.
24. An acetonide group was cleaved under the reported chlorination conditions.
25. Inhoffen, H. H.; Quinkert, G.; Schuetz, S.; Friedrich, G.; Tober, E. Chem. Ber. 1958, 91, 781; Lythgoe, B.; Roberts, D. A.; Waterhouse, I. J. Chem. Soc., Perkin Trans. I 1977, 2608.
26. Inhoffen, H. H.; Quinkert, G.; Schuetz, S.; Friedrich, G.; Tober, E. Chem. Ber. 1958, 91, 781; Lythgoe, B.; Roberts, D. A.; Waterhouse, I. J. Chem. Soc., Perkin Trans. I 1977, 2608.
27. Details of the preparation of 8 were presented in the Supporting Information.
28. Hu, Y.; Porco, J. A., Jr.; Labadie, J. W.; Gooding, O. W.; Trost, B. M. J. Org. Chem. 1998, 63, 4518.
29. -1, whose bands completely disappeared after acid cleavage.
30. The alkylation by means of the chloride salt of the Grignard reagent instead of the bromide salt 6 was unsuccessful. There are few reports using an alkoxy Grignard reagent in the alkylation at the 22-position on the steroid system, see: Nakagawa, M. Ph.D. thesis, University of Tokyo, 1993 and ref 9.