An expedient route to new spiroheterocycles: Synthesis and structural studies

European Journal of Organic Chemistry

Volumn , Issue 21, 2006, Pages 4805-4812

  Goubert, Marlène ^a   Canet, Isabelle ^a   Sinibaldi, Marie Eve ^a  

^a CNRS   (France)

Author keywords

Cyclization; Heterocycles; Nucleophilic substitution; Spiro compounds

Indexed keywords

EID: 33750879075     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600448     Document Type: Article

References (24)

1. For example, see: a) Y. Qtu, A. Hübener, H. Zhang, C. J. Moore, M. T. Fletcher, P. Hayes, K. Dettner, W. Francke, C. S. P. McErlean, W. Kitching, Synthesis 2000, 13, 1956-1978;
2. b) W. Francke, W. Kitching, Curr. Org. Chem. 2001, 5, 233-251.
3. For example, see: a) M. M. Faul, B. E. Huff, Chem. Rev. 2000, 100, 2407-2473;
4. b) J. A. Marshall, M. M. Yanik, J. Org. Chem. 2001, 66, 1373-1379.
5. For example, see: a) E. Hamel, Med. Res. Rev. 1996, 16, 207-231;
6. b) F. M. Uckun, C. Mao, A. O. Vassilev, H. Huang, S. T. Jan, Bioorg. Med. Chem. Lett. 2000, 10, 541-545;
7. c) O. Barun, K. Kumar, S. Sommer, A. Lgerak, T. U. Mayer, O. Müller, H. Waldmann, Eur. J. Org. Chem. 2005, 22, 4773-4788;
8. for inhibitors of the mitogenic activity of epidermal growth factors (EGF), see: d) T. Takahashi, H. Osada, H. Koshino, M. Sasaki, R. Onose, M. Nakakoshi, M. Yoshihama, K. Isono, J. Antibiot. 1992, 45, 1414-1419;
9. e) H. Takahashi, Y. Yamashita, H. Takaoka, J. Nakamura, M. Yoshihama, H. Osada, Oncol. Res. 1997, 9, 7-11;
10. for new apoptosis-inducing agents, see: f) S. Mitsuhashi, H. Shima, T. Kawamura, K. Kikuchi, M. Oikawa, A. Ichihara, H. Oikawa, Bioorg. Med. Chem. Lett. 1999, 9, 2007-2012;
11. g) K. Kikuchi, H. Shima, S. Mitsuhashi, M. Suzuki, H. Oikawa, Drugs Future 2000, 25, 501-507.
12. K. T. Mead, B. N. Brewer, Curr. Org. Chem. 2003, 7, 227-256.
13. a) E. M. Seward, E. Carlson, T. Harrison, K. R. Haworth, R. Herbert, F. J. Kelleher, M. M. Kurtz, J. Moselev, S. N. Owen, A. P. Owens, S. J. Sadowski, C. J. Swain, B. J. Williams, Bioorg. Med Chem. Lett. 2002, 12, 2515-2518;
14. b) J. D. Moseley, C. J. Swain, WO 97/30056, 1997.
15. P. T. Meinke, H. Mrozik, US 5162363, 1992.
16. A. Tursun, B. Aboab, I. Canet, M.-E. Sinibaldi, Tetrahedron Lett. 2005, 46, 2291-2294.
17. A. Tursun, B. Aboab, A.-S. Martin, M.-E. Sinibaldi, I. Canet, Synlett 2005, 15, 2397-2399.
18. a) P. M. Sher, R. D. Kronenthal, J. Labelled Compd. Radiopharm. 1997, 39, 21-28;
19. b) M. Hashimoto, Y. Hatanaka, J. Yang, J. Dhesi, G. D. Holman, Carbohydr. Res. 2001, 331, 119-127.
20. A.-H. Li, S. Moro, N. Forsyth, N. Melman, X.-D. Ji, K.-A. Jacobson, J. Med. Chem. 1999, 42, 706-721.
21. a) A. K. M. Anisuzzaman, L. N. Owen, J. Chem. Soc., C 1967, 11, 1021-1026;
22. b) P. C. Braga, US 4910220, 1988.
23. The physical data for (2R,6S,8R)-1a and (2R,6R,8S)-1b were in good agreement with those previously reported by M. Lemaire, G. Jeminet, J.-G. Gourcy, G. Dauphin, Tetrahedron: Asymmetry 1993, 4, 2101-2108.
24. R. J. Mears, H. E. Sailes, J. P. Watts, A. Whiting, J. Chem. Soc., Perkin Trans. 1 2000, 3250-3263.