Cascade cyclization, dipolar cycloaddition to bridged tricyclic amines related to the daphniphyllum alkaloids

Organic Letters

Volumn 13, Issue 6, 2011, Pages 1267-1269

  Coldham, Iain ^a,b   Burrell, Adam J M ^a,b   Guerrand, Hélène D S ^a,b   Oram, Niall ^a,b  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKALOID; AMINE; BUKITTINGGINE; DAPHNILACTONE B;

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

ALDEHYDES; ALKALOIDS; AMINES; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; SAXIFRAGACEAE;

EID: 79952585230     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102961x     Document Type: Article

References (34)

1. Kobayashi, J.; Kubota, T. Nat. Prod. Rep. 2009, 26, 936
2. Dong, M.; Zhang, M. L.; Shi, Q. W.; Gu, Y. C.; Kiyota, H. Curr. Org. Chem. 2009, 13, 646
3. Kobayashi, J.; Morita, H. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 2003; Vol. 60, pp 165 - 205.
4. Heathcock, C. H.; Hansen, M. M.; Ruggeri, R. B.; Kath, J. C. J. Org. Chem. 1992, 57, 2544
5. Heathcock, C. H.; Stafford, J. A. J. Org. Chem. 1992, 57, 2566
6. Heathcock, C. H.; Stafford, J. A.; Clark, D. L. J. Org. Chem. 1992, 57, 2575
7. Heathcock, C. H.; Ruggeri, R. B.; McClure, K. F. J. Org. Chem. 1992, 57, 2585
8. Heathcock, C. H.; Kath, J. C.; Ruggeri, R. B. J. Org. Chem. 1995, 60, 1120
9. Denmark, S. E.; Baiazitov, R. Y.; Nguyen, S. T. Tetrahedron 2009, 65, 6535
10. Denmark, S. E.; Nguyen, S. T.; Baiazitov, R. Y. Heterocycles 2008, 76, 143
11. Denmark, S. E.; Baiazitov, R. Y. J. Org. Chem. 2006, 71, 593
12. Ueda, M.; Walczak, M. A. A.; Wipf, P. Tetrahedron Lett. 2008, 49, 5986
13. Solé, D.; Urbaneja, X.; Bonjoch, J. Org. Lett. 2005, 7, 5461
14. Cordero-Vargas, A.; Urbaneja, X.; Bonjoch, J. Synlett 2007, 2379
15. Ikeda, S.; Shibuya, M.; Kanoh, N.; Iwabuchi, Y. Org. Lett. 2009, 11, 1833
16. Tanabe, K.; Fujie, A.; Ohmori, N.; Hiraga, Y.; Kojima, S.; Ohkata, K. Bull. Chem. Soc. Jpn. 2007, 80, 1597
17. Coldham, I.; Burrell, A. J. M.; White, L. E.; Adams, H.; Oram, N. Angew. Chem., Int. Ed. 2007, 46, 6159
18. Burrell, A. J. M.; Coldham, I.; Watson, L.; Oram, N.; Pilgram, C. D.; Martin, N. G. J. Org. Chem. 2009, 74, 2290
19. Burrell, A. J. M.; Coldham, I.; Oram, N. Org. Lett. 2009, 11, 1515
20. Burrell, A. J. M.; Watson, L.; Martin, N. G.; Oram, N.; Coldham, I. Org. Biomol. Chem. 2010, 8, 4530
21. For related chemistry, see: Pearson, W. H.; Stoy, P.; Mi, Y. J. Org. Chem. 2004, 69, 1919
22. Pearson, W. H.; Kropf, J. E.; Choy, A. L.; Lee, I. Y.; Kampf, J. W. J. Org. Chem. 2007, 72, 4135
23. Dondas, H. A.; Grigg, R.; Hadjisoteriou, M.; Markandu, J.; Thomas, W. A.; Kennewell, P. Tetrahedron 2000, 56, 10087
24. Coldham, I.; Jana, S.; Watson, L.; Pilgram, C. D. Tetrahedron Lett. 2008, 49, 5408
25. Yeom, H.-S.; Lee, J.-E.; Shin, S. Angew. Chem., Int. Ed. 2008, 47, 7040
26. Lévesque, F.; Bélanger, G. Org. Lett. 2008, 10, 4939
27. Coldham, I.; Jana, S.; Watson, L.; Martin, N. G. Org. Biomol. Chem. 2009, 7, 1674
28. Bestmann, H. J.; Koschatzky, K. H.; Platz, H.; Suess, J.; Vostrowsky, O.; Knauf, W.; Burghardt, G.; Schneider, I. Liebigs Ann. 1982, 1359
29. Whittaker, M.; McArthur, C. R.; Leznoff, C. C. Can. J. Chem. 1985, 63, 2844
30. Maruoka, K.; Imoto, H.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 4131
31. For a related sequence of reactions starting with an aldehyde-ester, see: Cheney, D. L.; Paquette, L. A. J. Org. Chem. 1989, 54, 3334
32. Coldham, I.; Hufton, R. Chem. Rev. 2005, 105, 2765
33. Burrell, A. J. M.; Coldham, I. Curr. Org. Synth. 2010, 7, 312
34. For a related sequence of reactions, see ref 3c.