Enantioselective synthesis of a key A-ring intermediate for the preparation of 1α,25-dihydroxyvitamin D3

Organic Letters

Volumn 13, Issue 1, 2011, Pages 86-89

  Chen, Yan ^a   Ju, Tong ^a  

^a TIANJIN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID; ACRYLIC ACID DERIVATIVE; DIHYDROXY VITAMIN D3; DIHYDROXY-VITAMIN D3; DRUG DERIVATIVE; VITAMIN D;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACRYLATES; CATALYSIS; MOLECULAR STRUCTURE; STEREOISOMERISM; VITAMIN D;

EID: 78650924690     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102586w     Document Type: Article

References (57)

1. Feldman, D., Pike, J. W., and Glorieux, F. H., Eds. Vitamin D, 2nd ed.; Elsevier Academic Press: New York, 2005.
2. DeLuca, H. F. Nutr. Rev. 2008, 66, s73-s87
3. Adorini, L.; Penna, G. Nat. Clin. Pract. Rheumatol. 2008, 4, 404-412
4. White, P.; Cooke, N. Trends Endocrinol. Metab. 2000, 11, 320-327
5. Hammes, S. R. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 21680-21700
6. Holick, M. F., Eds. Vitamin D; Humana Press: Totowa, NJ, 1999.
7. Bouillon, R.; Okamura, W. H.; Norman, A. W. Endocr. Rev. 1995, 16, 200-257
8. Carlberg, C.; Mourińo, A. Expert Opin. Ther. Patents 2003, 13, 761-772
9. DeLuca, H. F. J. Bone Miner. Metab. 1990, 8, 1-9
10. Bexkman, M. J.; DeLuca, H. F. Prog. Med. Chem. 1998, 35, 1-56
11. Stein, M. S.; Wark, J. D. Expert Opin. Investig. Drugs 2003, 12, 825-840
12. Zhu, G. D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877-1952
13. Dai, H.; Posner, G. H. Synthesis 1994, 1383-1398
14. Mathieu, C.; Adorini, L. Trends Mol. Med. 2002, 8, 174-179
15. Nagpal, S.; Na, S.; Rathnachalam, R. Endocr. Rev. 2005, 26, 662-687
16. Laverny, G.; Penna, G.; Uskokvic, M.; Marczak, S.; Maehr, H.; Jankowski, P.; Ceailles, C.; Vouros, P.; Smith, B.; Robinson, M.; Reddy, G. S.; Adorini, L. J. Med. Chem. 2009, 52, 2204-2213
17. Nakabayashi, M.; Yamada, S.; Yoshimoto, N.; Tanaka, T.; Igarashi, M.; Ikura, T.; Ito, N.; Makishima, M.; Tokiwa, H.; DeLuca, H. F.; Shimizu, M. J. Med. Chem. 2008, 51, 5320-5329
18. Norman, A. W.; Ishizuka, S.; Okamura, W. H. J. Steroid. Biochem. Mol. Biol. 2001, 76, 49-59
19. Sicinski, R. R.; Rotkiewicz, P.; Kolinski, A.; Sicinska, W.; Prahl, J. M. J. Med. Chem. 2002, 45, 3366-3380
20. Saito, N.; Suhara, Y.; Kurihara, M.; Fijishima, T.; Honzawa, S.; Takayanagi, H.; Kozono, T.; Matsumoto, M.; Ohmori, M.; Miyata, N.; Takayama, H.; Kittaka, A. J. Org. Chem. 2004, 69, 7463-7471
21. Glebocka, A.; Sicinski, R.; Plum, L. L.; Clagett-Dame, M.; DeLuca, H. F. J. Med. Chem. 2006, 49, 2909-2920
22. Sicinskil, R. R.; Glebocka, A.; Plum, L. A.; Deluca, H. F. J. Med. Chem. 2007, 50, 6154-6164
23. Kocienski, P. J.; Lythgoe, B.; Ruston, S. J. Chem. Soc., Perkin Trans. 1 1980, 1400-1404
24. Harrison, R. G.; Lythgoe, B.; Wright, P. W. Tetrahedron Lett. 1973, 14, 3649-3652
25. Okamura, W. H. Acc. Chem. Res. 1983, 16, 81-88
26. Mascareiias, J. L.; Sarandeses, L. A.; Castedo, L.; Mourińo, A. Tetrahedron 1991, 47, 3485-3498
27. Oves, D.; Ferrero, M.; Fernandez, S.; Gotor, V. J. Org. Chem. 2003, 68, 1154-1157
28. Rodriguez, R.; Ollivier, C.; Stantelli, M. Tetrahedron Lett. 2004, 45, 2289-2292
29. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 13, 3769-3772
30. Baggiolini, E. G.; Iacobelli, J. A.; Hennessy, B. M.; Batcho, A. D. J. Org. Chem. 1986, 51, 3098-3108
31. Okamura, W. H.; Aurrecoechea, J. M.; Gibbs, R. A.; Norman, A. W. J. Org. Chem. 1989, 54, 4072-4083
32. Castedo, L.; Mascareiias, J. L.; Mourińo, A. Tetrahedron Lett. 1987, 28, 2099-2102
33. Hatakeyama, S.; Numata, H.; Osanai, K.; Takano, S. J. Org, Chem. 1989, 54, 3515-3517
34. Bourque, L. E.; Cleary, P. A.; Woerpel, K. A. J. Am. Chem. Soc. 2007, 129, 12602-12603
35. Barbier, P.; Mohr, P.; Muler, M.; Masciadri, R. J. Org. Chem. 1998, 63, 6984-6989
36. Daniewski, A. R.; Garofalo, L. M.; Hutchings, S. D.; Kabat, M. M.; Liu, W.; Okabe, M.; Radiov, R.; Yiannikouros, G. P. J. Org. Chem. 2002, 67, 1580-1587
37. The absolute configuration of ester groups at C-1 and C-3 of 9 was confirmed by X-ray crystal analysis (see Supporting Information).
38. TBS was chosen as the protective group first, but it was found that the TBS ether 15 had no reaction when treated with the active form of formaldehyde 14. Considering if the steric hindrance of the TBS group might be the initial problem, we turned our attention to the MOM group.
39. 3 synthesis
40. Riveiros, R.; Rumbo, A.; Sarandeses, L. A.; Mourińo, A. J. Org. Chem. 2007, 72, 5477-5485
41. Reino, C. G.; Vitale, C.; Maestro, M.; Mourińo, A. Org. Lett. 2005, 7, 5885-5887
42. Moriaty, R. M.; Kim, J.; Brumer, H. Tetrahedron Lett. 1995, 36, 51-54
43. Nemoto, H.; Wu, X.; Kurobe, H.; Ihara, M.; Fukumoto, K.; Kametani, T. Tetrahedron Lett. 1983, 24, 4257-4260
44. Castedo, L.; Granja, J.; Maestro, M. A.; Mourińo, A. Tetrahedron Lett. 1987, 28, 4589-4590
45. Li, Y.; Feng, J.; Wang, W.; Chen, J.; Cao, X. J. Org. Chem. 2007, 72, 2344-2350
46. Maruoka, K.; Conception, A. B.; Murase, N.; Oishi, M.; Hirayama, N.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 3943-3949
47. The configuration of the new chiral center was not determined.
48. Suhara, Y.; Nihei, K.; Kurihara, M.; Kittaka, A.; Yamaguchi, K.; Fujishima, T.; Konno, K.; Miyata, N.; Takayama, H. J. Org. Chem. 2001, 66, 8760-8771
49. Takahashi, T.; Doi, T.; Hijikuro, I. J. Am. Chem. Soc. 2001, 123, 3716-3722
50. Saito, N.; Saito, H.; Anzai, M.; Yoshida, A.; Fujishima, T.; Takenouchi, K.; Miura, D.; Ishizuka, S.; Takayama, H.; Kittaka, A. Org. Lett. 2003, 5, 4859-4862
51. Saito, N.; Matsunaga, T.; Saito, H.; Anzai, M.; Takenouchi, K.; Miura, D.; Namekawa, J.; Ishizuka, S.; Kittaka, A. J. Med. Chem. 2006, 49, 7063-7075
52. Posner, G. H.; Woodard, B. T.; Grawford, K. R.; Peleg, S.; Brown, A. J.; Dolan, P.; Kensler, T. W. Bioorg. Med. Chem. 2002, 10, 2353-2365
53. Posner, G. H.; Cho, C. G.; Anjeh, T. E. N.; Johnson, N.; Horst, R. L.; Kobayashi, T.; Okano, T.; Tsugawa, N. J. Org. Chem. 1995, 60, 4617-4628
54. Posner, G. H.; Johnson, N. J. Org. Chem. 1994, 59, 7855-7861
55. Trost, B. M.; Dumas, J.; Villa, M. J. Am. Chem. Soc. 1992, 114, 9836-9845
56. Srikrishna, A.; Kumar, P. R. Tetrahrdron Lett. 2002, 43, 1109-1111
57. The approach from 22 to analogue 17 (R = α-Me) is continued in our lab. Herein, we wish to report this potential application of our new strategy.