Synthesis of vitamin D analogues with a 2-hydroxy-3-deoxy ring A

Tetrahedron Letters

Volumn 41, Issue 31, 2000, Pages 5861-5864

  Codesido, Eva María ^a   Cid, María Magdalena ^a   Castedo, Luis ^a   Mouriño, Antonio ^a   Granja, Juan R ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Asymmetric allylation; Vitamin D

Indexed keywords

PHOSPHINE OXIDE DERIVATIVE; VITAMIN D DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034729969     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00989-8     Document Type: Article

References (21)

1. (a) Bouillon, R.; Okamura, W. H.; Norman, A. W. Endocr. Rev. 1995, 16, 200-257;
2. (b) Vitamin D: Chemistry, Biology and Clinical Applications of the Steroid Hormone; Norman, A. W.; Bouillon, R.; Thomasset, M., Eds; Vitamin D Workshop; Riverside, CA, 1997.
3. Zhu, G.-D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877-1952.
4. Sicinski, R. R.; Prahl, J. M.; Smith, C. M.; DeLuca, H. F. J. Med. Chem. 1998, 41, 4662-4674, and references cited therein.
5. (a) Okano, T.; Tsugawa, N.; Masuda, S.; Takeuchi, A.; Kobayashi, T.; Takita, Y.; Nishii, Y. Biochem. Biophys. Res. Commun. 1989, 163, 1444-1449;
6. (b) Ono, Y.; Kawase, A.; Watanabe, H.; Shiraishi, A.; Takeda, S.; Higuchi, Y.; Sato, K.; Yamauchi, T.; Mikami, T.; Kato, M.; Tsugawa, N.; Okano, T.; Kubodera, N. Bioorg. Med. Chem. 1998, 6, 2517-2523.
7. For recent reports on the preparation of 2-hydroxyvitamin D analogues, see: (a) Doi, T.; Hijikuro, I.; Takahashi, T. J. Am. Chem. Soc. 1999, 121, 6749-6750; (b) Moriarty, R. M.; Brumer, H. Tetrahedron Lett. 1995, 36, 9265-9268; (c) Sicinski, R. R.; Perlman, K. L.; DeLuca, H. F. J. Med. Chem. 1994, 37, 3730-3738.
8. For recent reports on the preparation of 2-hydroxyvitamin D analogues, see: (a) Doi, T.; Hijikuro, I.; Takahashi, T. J. Am. Chem. Soc. 1999, 121, 6749-6750; (b) Moriarty, R. M.; Brumer, H. Tetrahedron Lett. 1995, 36, 9265-9268; (c) Sicinski, R. R.; Perlman, K. L.; DeLuca, H. F. J. Med. Chem. 1994, 37, 3730-3738.
9. For recent reports on the preparation of 2-hydroxyvitamin D analogues, see: (a) Doi, T.; Hijikuro, I.; Takahashi, T. J. Am. Chem. Soc. 1999, 121, 6749-6750; (b) Moriarty, R. M.; Brumer, H. Tetrahedron Lett. 1995, 36, 9265-9268; (c) Sicinski, R. R.; Perlman, K. L.; DeLuca, H. F. J. Med. Chem. 1994, 37, 3730-3738.
10. Daniel, D.; Middleton, R.; Henry, H. L.; Okamura, W. H. J. Org. Chem. 1996, 61, 5617-5626.
11. Preliminary results on the synthesis of racemic A-ring 9 were presented as a poster in the VIth ISBOC, 1997, Biarritz, France.
12. 2, 62.83 MHz) δ: 144.7, 143.6, 139.7, 122.0, 119.5, 115.8, 72.5, 71.6, 58.5, 58.2, 47.7, 46.9, 46.3, 42.4, 38.3, 38.0, 37.3, 35.3, 31.0, 30.9, 30.8, 29.5, 25.5, 24.2, 22.7, 20.5, 13.5.
13. Mascareñas, J. L.; García, A. M.; Castedo, L.; Mouriño, A. Tetrahedron Lett. 1992, 33, 4365-4368.
14. (a) Lythgoe, B. Chem. Soc. Rev. 1980, 9, 449-475;
15. (b) Baggiolini, E. G.; Iacobelli, J. A.; Hennessy, B. M.; Batcho, A. D.; Sereno, J. F.; Uskokovic, M. R. J. Org. Chem. 1986, 51, 3098-3108.
16. For convenience, steroid numbering is used.
17. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293.
18. 3).
19. Gauthier Jr., D. R.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363-2365.
20. The absolute configuration of (4S)-6 was inferred from the effects of the phenyl groups of the R and S methoxyphenylacetic esters on the chemical shift of the C3 and C5 protons. Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370-2374.
21. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467-8468.