Novel synthesis of a 1,3,5-trioxazatriquinane skeleton using a nitrogen clamp

Organic Letters

Volumn 11, Issue 3, 2009, Pages 539-542

  Nagase, Hiroshi ^a   Watanabe, Akio ^a   Harada, Masaya ^a   Nakajima, Mayumi ^b   Hasebe, Ko ^b   Mochizuki, Hidenori ^b   Yoza, Kenji ^c   Fujii, Hideaki ^a  

^a KITASATO UNIVERSITY   (Japan)

^b TORAY INDUSTRIES INC   (Japan)

^c BRUKER AXS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FUSED HETEROCYCLIC RINGS; NALTREXONE; NITROGEN; OXAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NALTREXONE; NITROGEN; OXAZOLES;

EID: 60849139457     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8024988     Document Type: Article

References (17)

1. (a) Portoghese, P. S.; Sultana, M.; Nagase, H.; Takemori, A. E. J. Med. Chem. 1988, 31, 281-282.
2. (b) Portoghese, P. S.; Nagase, H.; Lipkowski, A. W.; Larson, D. L.; Takemori, A. E. J. Med. Chem. 1988, 31, 836-841.
3. (c) Portoghese, P. S.; Nagase, H.; Takemori, A. E. J. Med. Chem. 1988, 31, 1344-1347.
4. (d) Portoghese, P. S.; Nagase, H.; Maloney-Huss, K. E.; Lin, C.-E.; Takemori, A. E. J. Med. Chem. 1991, 34, 1715-1720.
5. (e) Nagase, H.; Hayakawa, J.; Kawamura, K.; Kawai, K.; Takezawa, Y.; Matsuura, H.; Tajima, C.; Endo, T. Chem. Pharm. Bull. 1998, 46, 366-369.
6. (f) Fujii, H.; Nagase, H. Curr. Med. Chem. 2006, 13, 1109-1118.
7. (a) Nagase, H.; Abe, A.; Portoghese, P. S. J. Org. Chem. 1989, 54, 4120-4125.
8. (b) Fujii, H.; Mizusuna, A.; Tanimura, R.; Nagase, H. Heterocycles 1997, 45, 2109-2112.
9. (c) Fujii, H.; Hirano, N.; Uchiro, H.; Kawamura, K.; Nagase, H. Chem. Pharm. Bull. 2004, 52, 747-750.
10. (d) Watanabe, A.; Kai, T.; Nagase, H. Org. Lett. 2006, 8, 523-526.
11. (e) Osa, Y.; Ida, Y.; Furuhata, K.; Nagase, H. Heterocycles 2006, 69, 271-282.
12. (f) Nagase, H.; Watanabe, A.; Nemoto, T.; Yamamoto, N.; Osa, Y.; Yoza, N.; Kai, T. Tetrahedoron Lett. 2007, 48, 2547-2553.
13. Fujii, H.; Watanabe, A.; Nemoto, T.; Narita, M.; Miyoshi, K.; Nakaraura, A.; Suzuki, T.; Nagase, H. Bioorg. Med. Chem. Lett. 2009, 19, 438-441.
14. Determination of the stereochemistry of trimers 14, 16, and 18 was described in the Supporting Information.
15. (a) Rios, C. D.; Joran, B. A.; Gomes, I.; Devi, L. A. Pharmacol. Ther. 2001, 92, 71-87.
16. (b) Levac, B. A. R.; O'Dowd, B. F.; George, S. R. Curr. Opin. Pharmacol. 2002, 2, 76-81.
17. Contreras, J.-M.; Bourguignon, J.-J. In The practice of Medicinal Chemistry, 2nd ed.; Wermuth, C. G., Ed.; Academic press: London, 2003; pp 251-273.