Tandem oxidative dearomatization/intramolecular Diels-Alder reaction for construction of the tricyclic core of palhinine A

Organic Letters

Volumn 14, Issue 9, 2012, Pages 2293-2295

  Zhao, Changgui ^a   Zheng, Huaiji ^a   Jing, Peng ^a   Fang, Bowen ^a   Xie, Xingang ^a   She, Xuegong ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; PALHININE A;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; LYCOPODIUM; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALKALOIDS; CYCLIZATION; LYCOPODIUM; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 84860633086     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol3007138     Document Type: Article

References (53)

1. Ayer, W. A.; Trifonov, L. S. In The Alkaloids, Vol. 45; Cordell, G. A., Brossi, A., Eds.; Academic Press: New York, 1994; p 233.
2. Ma, X.; Gang, D. R. Nat. Prod. Rep. 2004, 21, 752
3. Kobayashi, J.; Morita, H. In The Alkaloids, Vol. 61; Cordell, G. A, Ed.; Academic Press: New York, 2005; p 1.
4. Hirasawa, Y.; Kobayashi, J.; Morita, H. Heterocycles 2009, 77, 679
5. Kitajima, M.; Takayama, H. Lycopodium Alkaloids: Isolation and Asymmetric Synthesis in Topics in Current Chemistry; Knölker, H.-J., Ed.; Springer: Berlin, 2012; Vol. 309/2012, pp 1-31.
6. Beshore, D. C.; Smith, A. B. J. Am. Chem. Soc. 2008, 130, 13778
7. Nilsson, B. L.; Overman, L. E.; Alaniz, J. R.; Rohde, J. M. J. Am. Chem. Soc. 2008, 130, 11297
8. Chandra, A.; Pigza, J. A.; Han, J.-S.; Mutnick, D.; Johnston, J. N. J. Am. Chem. Soc. 2009, 131, 3470
9. Yang, H.; Carter, R. G. J. Org. Chem. 2010, 75, 4929
10. Laemmerhold, K. M.; Breit, B. Angew. Chem., Int. Ed. 2010, 49, 2367
11. Bisai, V.; Sarpong, R. Org. Lett. 2010, 12, 2551
12. Altman, R. A.; Nilsson, B. L.; Overman, L. E.; Read deAlaniz, J.; Rohde, J. M.; Taupin, V. J. Org. Chem. 2010, 75, 7519
13. Cheng, X.; Waters, S. P. Org. Lett. 2010, 12, 205
14. Wolfe, B. H.; Libby, A. H.; Al-awar, R. S.; Foti, C. J.; Comins, D. L. J. Org. Chem. 2010, 75, 8564
15. Nakamura, Y.; Burke, A. M.; Kotani, S.; Ziller, J. W.; Rychnovsky, S. D. Org. Lett. 2010, 12, 72
16. Liau, B. B.; Shair, M. D. J. Am. Chem. Soc. 2010, 132, 9594
17. Yuan, C.; Chang, C.-T.; Axelrod, A.; Siegel, D. J. Am. Chem. Soc. 2010, 132, 5924
18. Fischer, D. F.; Sarpong, R. J. Am. Chem. Soc. 2010, 132, 5926
19. Nishimura, T.; Unni, A. K.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. 2011, 133, 418
20. Linghu, X.; Kennedy-Smith, J. J.; Toste, F. D. Angew. Chem., Int. Ed. 2007, 46, 7671
21. Kozak, J. A.; Dake, G. R. Angew. Chem., Int. Ed. 2008, 47, 4221
22. Nakayama, A.; Kogure, N.; Kitajima, M.; Takayama, H. Org. Lett. 2009, 11, 5554
23. Ramharter, J.; Weinstabl, H.; Mulzer, J. J. Am. Chem. Soc. 2010, 132, 14338
24. Canham, D. S.; France, M. J.; Overman, L. E. J. Am. Chem. Soc. 2010, 132, 7876
25. Otsuka, Y.; Inagaki, F.; Mukai, C. J. Org. Chem. 2010, 75, 3420
26. Jung, M. E.; Chang, J. J. Org. Lett. 2010, 12, 2962
27. Nakayama, A.; Kogure, N.; Kitajima, M.; Takayama, H. Angew. Chem., Int. Ed. 2011, 50, 8025
28. Yang, Y.-R.; Shen, L.; Huang, J.-Z.; Xu, T.; Wei, K. J. Org. Chem. 2011, 76, 3684
29. Zhang, X. M.; Tu, Y. Q.; Zhang, F. M.; Shao, H.; Meng, X. Angew. Chem., Int. Ed. 2011, 50, 3916
30. Li, H.; Wang, X.; Lei, X. Angew. Chem., Int. Ed. 2012, 51, 491
31. Zhao, F.; Sun, Q.; Yang, F.; Hu, G.; Luo, J.; Tang, G.; Wang, Y.; Long, C. Org. Lett. 2010, 12, 3922
32. Magdziak, D.; Meek, S. J.; Pettus, T. R. R. Chem. Rev. 2004, 104, 1383
33. Shiao, H.-Y.; Hsieh, H.-P.; Liao, C.-C. Org. Lett. 2008, 10, 3
34. Nicolaou, K. C.; Toh, Q.-Y.; Chen, D. Y.-K. J. Am. Chem. Soc. 2008, 130, 11292
35. Gao, S.-Y.; Chittimalla, S. K.; Chuang, G. J.; Liao, C.-C. J. Org. Chem. 2009, 74, 1632
36. Dory, Y. L.; Roy, A.-L.; Soucy, P.; Deslongchamps, P. Org. Lett. 2009, 11, 1197
37. Morton, J. G. M.; Draghici, C.; Kwon, L. D.; Njardarson, J. T. Org. Lett. 2009, 11, 4492
38. Snyder, S. A.; Kontes, F. J. Am. Chem. Soc. 2009, 131, 1745
39. Krawczuk, P. J.; Schöne, N.; Baran, P. S. Org. Lett. 2009, 11, 21
40. Gong, J.; Lin, G.; Sun, W.; Li, C.-C.; Yang, Z. J. Am. Chem. Soc. 2010, 132, 16745
41. Gu, Z.; Zakarian, A. Org. Lett. 2011, 13, 5
42. Boger, D. L.; Hong, J.; Hikota, M.; Ishida, M. J. Am. Chem. Soc. 1999, 121, 2471
43. Sha, C.-K.; Liao, H.-W.; Cheng, P.-C.; Yen, S.-C. J. Org. Chem. 2003, 68, 8704
44. Sha, C.-K.; Santhosh, K. C.; Lih, S.-H. J. Org. Chem. 1998, 63, 2699
45. Dowd, P.; Zhang, W.; Mahmood, K. Tetrahedron. 1995, 51, 39
46. Curran, D. P.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140
47. Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741
48. Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611
49. Schrwk, R. R. J. Am. Chem. Soc. 1976, 98, 5399
50. Mulzer, J.; Mantoulidis, A.; Ohler, E. J. Org. Chem. 2000, 65, 7456
51. Demuth, M. Helv. Chim. Acta 1978, 61, 3136
52. Moher, E. D.; Collins, J. L.; Grieco, P. A. J. Am. Chem. Soc. 1992, 114, 2164
53. Ciufolini, M. A.; Zhu, S. J. Org. Chem. 1998, 63, 1668