Cation Radical [3+2] Cycloaddition of Chalcone Epoxides: A Facile Synthesis of Highly Substituted Tetrahydrofurans

Synlett

Volumn , Issue 2, 2004, Pages 251-254

  Huo, Congde ^a   Jia, Xiaodong ^a   Zhang, Wei ^a   Yang, Li ^a   Lü, Jianming ^a   Liu, Zhong Li ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Cation radical; Cycloaddition; Epoxides; Tetrahydrofurans

Indexed keywords

ALKENE DERIVATIVE; CHALCONE; EPOXIDE; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CYCLOADDITION; ELECTRON; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR MECHANICS; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 1242273679     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-44966     Document Type: Article

References (38)

1. (a) Moody, C. J.; Davies, M. In Studies in Natural Product Chemistry, Vol. 10; Ata-ur-Rahman, , Ed.; Elsevier: Amsterdam, 1992, 201.
2. (b) Erickson, K. L. In Marine Natural Products, Vol. 5; Scheuer, P. J., Ed.; Academic Press: New York, 1983, Chap. 4, 131.
3. (c) Kim, E.-J.; Tian, F.; Woo, M.-H. J. Nat. Prod. 2000, 63, 1503.
4. (d) Kobayashi, J.; Kubota, T.; Endo, T.; Tsuda, M. J. Org. Chem. 2001, 66, 134.
5. (T) (a) Gottlieb, O. R. In New Natural Products and Plant Drugs with Pharmacological, Biological or Therapeutical Activity; Springer-Verlag: Berlin/Heidelberg, 1987, 227.
6. (b) Oberlies, N. H.; Jones, J. L.; Corbett, T. H.; Fotopoulos, S. S.; McLaughlin, J. L. Cancer Lett. 1995, 96, 55.
7. For reviews, see: (a) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (b) Semple, J. E.; Joullie, M. M. Heterocycles 1980, 14, 1825. (c) Harmange, J. C.; Figadére, B. Tetrahedron: Asymmetry 1993, 1711. (d) Postema, M. H. D. Tetrahedron 1992, 48, 8545.
8. For reviews, see: (a) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (b) Semple, J. E.; Joullie, M. M. Heterocycles 1980, 14, 1825. (c) Harmange, J. C.; Figadére, B. Tetrahedron: Asymmetry 1993, 1711. (d) Postema, M. H. D. Tetrahedron 1992, 48, 8545.
9. For reviews, see: (a) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (b) Semple, J. E.; Joullie, M. M. Heterocycles 1980, 14, 1825. (c) Harmange, J. C.; Figadére, B. Tetrahedron: Asymmetry 1993, 1711. (c) Postema, M. H. D. Tetrahedron 1992, 48, 8545.
10. For reviews, see: (a) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (b) Semple, J. E.; Joullie, M. M. Heterocycles 1980, 14, 1825. (c) Harmange, J. C.; Figadére, B. Tetrahedron: Asymmetry 1993, 1711. (d) Postema, M. H. D. Tetrahedron 1992, 48, 8545.
11. For recent examples, see: (a) Ericsson, C.; Engman, L. Org. Lett. 2001, 3, 3459. (b) Vares, L.; Rein, T. J. Org. Chem. 2002, 67, 7226. (c) Pearson, A. J.; Mesaros, E. F. Org. Lett. 2001, 3, 2665. (d) Kamimura, A.; Mitsudera, H.; Matsuura, K.; Omata, Y.; Shirai, M.; Yokoyama, S.; Kakehi, A. Tetrahedron 2002, 58, 2605. (e) Bottex, M.; Cavicchioli, M.; Hartmann, B.; Monteiro, N.; Balme, G. J. Org. Chem. 2001, 66, 175. (f) Liu, B.; Duan, S.; Sutterer, A. C.; Moeller, K. D. J. Am. Chem. Soc. 2002, 124, 10101.
12. For recent examples, see: (a) Ericsson, C.; Engman, L. Org. Lett. 2001, 3, 3459. (b) Vares, L.; Rein, T. J. Org. Chem. 2002, 67, 7226. (c) Pearson, A. J.; Mesaros, E. F. Org. Lett. 2001, 3, 2665. (d) Kamimura, A.; Mitsudera, H.; Matsuura, K.; Omata, Y.; Shirai, M.; Yokoyama, S.; Kakehi, A. Tetrahedron 2002, 58, 2605. (e) Bottex, M.; Cavicchioli, M.; Hartmann, B.; Monteiro, N.; Balme, G. J. Org. Chem. 2001, 66, 175. (f) Liu, B.; Duan, S.; Sutterer, A. C.; Moeller, K. D. J. Am. Chem. Soc. 2002, 124, 10101.
13. For recent examples, see: (a) Ericsson, C.; Engman, L. Org. Lett. 2001, 3, 3459. (b) Vares, L.; Rein, T. J. Org. Chem. 2002, 67, 7226. (c) Pearson, A. J.; Mesaros, E. F. Org. Lett. 2001, 3, 2665. Kamimura, A.; Mitsudera, H.; Matsuura, K.; Omata, Y.; Shirai, M.; Yokoyama, S.; Kakehi, A. Tetrahedron 2002, 58, 2605. (e) Bottex, M.; Cavicchioli, M.; Hartmann, B.; Monteiro, N.; Balme, G. J. Org. Chem. 2001, 66, 175. (f) Liu, B.; Duan, S.; Sutterer, A. C.; Moeller, K. D. J. Am. Chem. Soc. 2002, 124, 10101.
14. For recent examples, see: (a) Ericsson, C.; Engman, L. Org. Lett. 2001, 3, 3459. (b) Vares, L.; Rein, T. J. Org. Chem. 2002, 67, 7226. (c) Pearson, A. J.; Mesaros, E. F. Org. Lett. 2001, 3, 2665. (d) Kamimura, A.; Mitsudera, H.; Matsuura, K.; Omata, Y.; Shirai, M.; Yokoyama, S.; Kakehi, A. Tetrahedron 2002, 58, 2605. (e) Bottex, M.; Cavicchioli, M.; Hartmann, B.; Monteiro, N.; Balme, G. J. Org. Chem. 2001, 66, 175. (f) Liu, B.; Duan, S.; Sutterer, A. C.; Moeller, K. D. J. Am. Chem. Soc. 2002, 124, 10101.
15. For recent examples, see: (a) Ericsson, C.; Engman, L. Org. Lett. 2001, 3, 3459. (b) Vares, L.; Rein, T. J. Org. Chem. 2002, 67, 7226. (c) Pearson, A. J.; Mesaros, E. F. Org. Lett. 2001, 3, 2665. (d) Kamimura, A.; Mitsudera, H.; Matsuura, K.; Omata, Y.; Shirai, M.; Yokoyama, S.; Kakehi, A. Tetrahedron 2002, 58, 2605. (e) Bottex, M.; Cavicchioli, M.; Hartmann, B.; Monteiro, N.; Balme, G. J. Org. Chem. 2001, 66, 175. (f) Liu, B.; Duan, S.; Sutterer, A. C.; Moeller, K. D. J. Am. Chem. Soc. 2002, 124, 10101.
16. For recent examples, see: (a) Ericsson, C.; Engman, L. Org. Lett. 2001, 3, 3459. (b) Vares, L.; Rein, T. J. Org. Chem. 2002, 67, 7226. (c) Pearson, A. J.; Mesaros, E. F. Org. Lett. 2001, 3, 2665. (d) Kamimura, A.; Mitsudera, H.; Matsuura, K.; Omata, Y.; Shirai, M.; Yokoyama, S.; Kakehi, A. Tetrahedron 2002, 58, 2605. (e) Bottex, M.; Cavicchioli, M.; Hartmann, B.; Monteiro, N.; Balme, G. J. Org. Chem. 2001, 66, 175. (f) Liu, B.; Duan, S.; Sutterer, A. C.; Moeller, K. D. J. Am. Chem. Soc. 2002, 124, 10101.
17. Shim, J.-G.; Yamamoto, Y. J. Org. Chem. 1998, 63, 3067.
18. Feldman, K. S.; Fisher, T. E. Tetrahedron 1989, 45, 2969.
19. (a) Jin, M.-Z.; Yang, L.; Wu, L.-M.; Liu, Y.-C.; Liu, Z.-L. Chem. Commun. 1998, 2451.
20. (b) Mao, Y. Z.; Jin, M. Z.; Liu, Z.-L.; Wu, L. M. Org. Lett. 2000, 2, 741.
21. (c) Jin, M.-Z.; Zhang, D.; Yang, L.; Liu, Y.-C.; Liu, Z.-L. Tetrahedron Lett. 2000, 41, 7357.
22. (d) Zhang, W.; Jia, X.; Yang, L.; Liu, Z.-L. Tetrahedron Lett. 2002, 43, 9433.
23. (e) Zhang, J.; Jin, M.-Z.; Zhang, W.; Yang, L.; Liu, Z.-L. Tetrahedron Lett. 2002, 43, 9687.
24. (a) Bauld, N. L. Tetrahedron 1989, 45, 5307.
25. (b) Bauld, N. L.; Bellville, D. J.; Harirchian, B.; Lorenz, K. T.; Pabon, P. A. Jr.; Reynolds, D. W.; Wirth, D. D.; Chiou, H.-S.; Marsh, B. K. Acc. Chem. Res. 1987, 20, 371.
26. (c) Schmittel, M.; Woehrle, C.; Bohn, I. Acta Chem. Scand. 1997, 51, 151.
27. Jia, X.; Lin, H.; Huo, C.; Zhang, W.; Lü, J.; Yang, L.; Zhao, G.; Liu, Z.-L. Synlett 2003, 1707.
28. 3): δ = 30.9 (Me), 45.2 (C-3), 48.3 (C-4), 55.2 (MeO), 86.0 (C-2), 86.3 (C-5), 114.0 (Ar), 124.8 (Ph), 126.7 (Ph), 128.0 (Bz), 128.3 (Bz), 128.8 (Ph), 129.3 (Ar). 131.6 (Ar), 133.0 (Bz), 136.2 (Bz), 147.1 (Ph), 158.4 (Ar), 196.6 (C=O).
29. (a) Mlcoch, J.; Steckhan, E. Tetrahedron Lett. 1987, 28, 1081.
30. (b) Habert, U.; Steckhan, E.; Blechert, S.; Wiest, O. Chem.-Eur. J. 1999, 5, 2859.
31. (a) Hasegawa, E.; Ishiyama, K.; Kato, T.; Horaguchi, T.; Shimizu, T. J. Org. Chem. 1992, 57, 5352.
32. (b) Hasegawa, E.; Kato, T.; Kitazume, T.; Yanagi, K.; Hasegawa, K.; Horaguchi, T. Tetrahedron Lett 1996, 39, 7079.
33. (c) Hasegawa, E.; Chiba, N.; Nakajima, A.; Suzuki, K.; Yoneoka, A.; Iwaya, K. Synthesis 2001, 1248.
34. (d) Hasegawa, E.; Ishiyama, K.; Kashiwazaki, H.; Horaguchi, T.; Shimizu, T. Tetrahedron Lett. 1990, 31, 4045.
35. (e) Cossy, J.; Ibhi, B. S.; Aclinou, P. Tetrahedron 1991, 47, 7775.
36. (f) Kato, H.; Tezuka, H.; Yamaguchi, K.; Nowada, K.; Nakamura, Y. J. Chem. Soc., Perkin Trans. 1 1978, 1029.
37. (g) Lee, G. A. J. Org. Chem. 1978, 43, 4256.
38. (h) Hallet, P.; Muzart, J.; Pete, J. P. J. Org. Chem. 1981, 46, 4275.