Total synthesis of (-)-hippodamine by stereocontrolled construction of azaphenalene skeleton based on extended one-pot asymmetric azaelectrocyclization

Organic Letters

Volumn 15, Issue 11, 2013, Pages 2758-2761

  Fujita, Shintaro ^a   Sakaguchi, Taku ^a   Kobayashi, Toyoharu ^a,b   Tsuchikawa, Hiroshi ^a,c   Katsumura, Shigeo ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

^c OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84879228864     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4010917     Document Type: Article

References (30)

1. Happ, G. M.; Eisner, T. Science 1961, 134, 329
2. Tursch, B.; Daloze, D.; Braekman, J. C.; Hootele, C.; Pasteels, J. M. Tetrahedron 1975, 31, 1541
3. Tursch, B.; Daloze, D.; Dupont, M.; Pasteels, J. M.; Tricot, M. C. Experientia 1971, 27, 1380
4. Tursch, B.; Daloze, D.; Pasteels, J. M.; Cravador, A.; Braekman, J. C.; Hootele, C.; Zimmermann, D. Bull. Soc. Chim. Belg. 1972, 81, 649
5. Tursch, B.; Daloze, D.; Braekman, J. C.; Hootele, C.; Cravador, A.; Losman, D.; Karlsson, R. Tetrahedron Lett. 1974, 409
6. Ayer, W. A.; Dawe, R.; Eisner, R. A.; Furuichi, K. Can. J. Chem. 1976, 54, 473
7. Mueller, R. H.; Thompson, M. E.; DiPardo, R. M. J. Org. Chem. 1984, 49, 2271
8. Gerasyuto, A. I.; Hsung, R. P. J. Org. Chem. 2007, 72, 2476
9. Díaz-Gavilán, M.; Galloway, W. R. J. D.; O'Connell, K. M. G.; Hodkingson, J. T.; Spring, D. R. Chem. Commun. 2010, 46, 776
10. Ayer, W. A.; Furuichi, K. Can. J. Chem. 1976, 54, 1494
11. Mueller, R. H.; Thompson, M. E. Tetrahedron Lett. 1979, 1991
12. Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032
13. Yue, C.; Nicolay, J. F.; Royer, J.; Husson, H. P. Tetrahedron 1994, 50, 3139
14. Takahata, H.; Ouchi, H.; Ichinose, M.; Nemoto, H. Org. Lett. 2002, 4, 3459
15. Gerasyuto, A. I.; Hsung, R. P. Org. Lett. 2006, 8, 4899
16. Mueller, R. H.; Thompson, M. E. Tetrahedron Lett. 1980, 1093
17. Rejzek, M.; Stockman, R. A.; Hughes, D. L. Org. Biomol. Chem. 2005, 3, 73
18. Kobayashi, T.; Nakashima, M.; Hakogi, T.; Tanaka, K.; Katsumura, S. Org. Lett. 2006, 8, 3809
19. Kobayashi, T.; Hasegawa, F.; Tanaka, K.; Katsumura, S. Org. Lett. 2006, 8, 3813
20. Kobayashi, T.; Takeuchi, K.; Miwa, J.; Tsuchikawa, H.; Katsumura, S. Chem. Commun. 2009, 3363
21. Li, Y.; Kobayashi, T.; Katsumura, S. Tetrahedron Lett. 2009, 50, 4482
22. Sakaguchi, T.; Kobayashi, S.; Katsumura, S. Org. Biomol. Chem. 2011, 9, 257
23. Kobayashi, T.; Hasegawa, F.; Hirose, Y.; Tanaka, K.; Mori, H.; Katsumura, S. J. Org. Chem. 2012, 77, 1812
24. Suga, S.; Yamada, D.; Yoshida, J. Chem. Lett. 2010, 39, 404
25. Tanaka, K.; Katsumura, S. J. Am. Chem. Soc. 2002, 124, 9660
26. Tanaka, K.; Mori, H.; Yamamoto, M.; Katsumura, S. J. Org. Chem. 2001, 66, 3099
27. Kobayashi, T.; Tanaka, K.; Miwa, J.; Katsumura, S. Tetrahedron: Asymmetry 2004, 15, 185
28. Ueno, Y.; Tanaka, C.; Okawara, M. Chem. Lett. 1983, 795
29. Suginome, H.; Umeda, H.; Masamune, T. Tetrahedron Lett. 1970, 11, 4571
30. Lebrun, B.; Braekman, J. C.; Daloze, D. Magn. Reson. Chem. 1999, 37, 60