Highly efficient synthesis of 3a,6a-dihydrofuro[2,3-b]furans via a novel bicyclization

Organic Letters

Volumn 15, Issue 3, 2013, Pages 456-459

  Shu, Wen Ming ^a   Yang, Yan ^a   Zhang, Dong Xue ^a   Wu, Liu Ming ^a   Zhu, Yan Ping ^a   Yin, Guo Dong ^b   Wu, An Xin ^a  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

^b HUBEI NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; FUSED HETEROCYCLIC RINGS; KETONE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

BICYCLO COMPOUNDS, HETEROCYCLIC; CATALYSIS; CYCLIZATION; FURANS; KETONES; MOLECULAR STRUCTURE;

EID: 84873334224     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400016c     Document Type: Article

References (33)

1. Pezechk, M.; Brunetiere, A. P.; Lallemand, J. Y. Tetrahedron Lett. 1986, 27, 3715-3718
2. Gowrisankar, S.; Lee, K. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2006, 37, 929-932
3. Gui, J.; Wang, D.; Tian, W. Angew. Chem., Int. Ed. 2011, 50, 7093-7096
4. Sridhar, P. R.; Reddy, G. M.; Seshadri, K. Eur. J. Org. Chem. 2012, 6228-6235
5. Bullock, E.; Roberts, J. C.; Underwood, J. G. J. Chem. Soc. (Resumed) 1962, 4179-4183
6. Rodricks, J. V. J. Agric. Food Chem. 1969, 17, 457-461
7. Raney, K. D.; Shimada, T.; Kim, D. H.; Groopman, J. D.; Harris, T. M.; Guengerich, F. P. Chem. Res. Toxicol. 1992, 5, 202-210
8. Iyer, R. S.; Coles, B. F.; Raney, K. D.; Thier, R.; Guengerich, F. P.; Harris, T. M. J. Am. Chem. Soc. 1994, 116, 1603-1609
9. Udwary, D. W.; Casillas, L. K.; Townsend, C. A. J. Am. Chem. Soc. 2002, 124, 5294-5303
10. Lee, N. A.; Wang, S.; Allan, R. D.; Kennedy, I. R. J. Agric. Food. Chem. 2004, 52, 2746-2755
11. Bren, U.; Guengerich, F. P.; Mavri, J. Chem. Res. Toxicol. 2007, 20, 1134-1140
12. Jubert, C.; Mata, J.; Bench, G.; Dashwood, R.; Pereira, C.; Tracewell, W.; Turteltaub, K.; Williams, D.; Bailey, G. Cancer Prev. Res. 2009, 2, 1015-1022
13. Marino, J. P.; Kieler, K. A.; Kim, M.-W. Tetrahedron 2011, 67, 837-841
14. Kornsakulkarn, J.; Saepua, S.; Srichomthong, K.; Supothina, S.; Thongpanchang, C. Tetrahedron 2012, 68, 8480-8486
15. Fujimaki, T.; Nagase, H.; Yamaguchi, R.; Kawai, K.; Otomasu, H. Chem. Pharm. Bull. 1985, 33, 2663
16. Aran, V. J.; Martin, N.; Seoane, C.; Soto, J. L.; Sanz-Aparicio, J.; Florencio, F. J. Org. Chem. 1988, 53, 5341-5343
17. Makosza, M.; Niyazimbetov, M. Synlett 1992, 417-418
18. Schank, K.; Lick, C. Synthesis 1983, 392-395
19. Pirrung, M. C.; Zhang, J.; McPhail, A. T. J. Org. Chem. 1991, 56, 6269-6271
20. McCarthy, N.; McKervey, M. A.; Ye, T.; McCann, M.; Murphy, E.; Doyle, M. P. Tetrahedron Lett. 1992, 33, 5983-5986
21. Pirrung, M. C.; Zhang, J. Tetrahedron Lett. 1992, 33, 5987-5990
22. Müller, P.; Fernandez, D. Helv. Chim. Acta 1995, 78, 947-958
23. Davies, H. M. L.; Calvo, R. L. Tetrahedron Lett. 1997, 38, 5623-5626
24. Yin, B.-L.; Zeng, G.-H.; Cai, C.-B.; Ji, F.-H.; Huang, L.; Li, Z.-R.; Jiang, H.-F. Org. Lett. 2012, 14, 616-619
25. Gao, M.; Yang, Y.; Wu, Y.-D.; Deng, C.; Cao, L.-P.; Meng, X.-G.; Wu, A.-X. Org. Lett. 2010, 12, 1856-1859
26. Yang, Y.; Gao, M.; Wu, L.-M.; Deng, C.; Zhang, D.-X.; Gao, Y.; Zhu, Y.-P.; Wu, A.-X. Tetrahedron 2011, 67, 5142-5149
27. Gao, M.; Yang, Y.; Wu, Y.-D.; Deng, C.; Shu, W.-M.; Zhang, D.-X.; Cao, L.-P.; She, N.-F.; Wu, A.-X. Org. Lett. 2010, 12, 4026-4029
28. Yin, G. D.; Gao, M.; She, N. F.; Hu, S. L.; Wu, A. X.; Pan, Y. J. Synthesis 2007, 3113-3116
29. Kornblum, N.; Powers, J. W.; Anderson, G. J.; Jones, W. J.; Larson, H. O.; Levand, O.; Weaver, W. M. J. Am. Chem. Soc. 1957, 79, 6562-6562
30. Knoevenagel, E. Chem. Dtsch. Ber. Ges. 1896, 29, 172-174
31. Shrestha-Dawadi, P. B.; Lugtenburg, J. Eur. J. Org. Chem. 2007, 1294-1300
32. Dawadi, P. B. S.; Lugtenburg, J. Global J. Sci. Frontier Res. 2012, 12, 23-36
33. Ikeguchi, M.; Sawaki, M.; Yoshii, H.; Maeda, K.; Morishima, Y. J. Pest. Sci. 2000, 25, 107-116