Catalytic asymmetric assembly of C3-monosubstituted chiral carbazolones and concise formal synthesis of (-)-aspidofractinine: Application of enantioselective pd-catalyzed decarboxylative protonation of carbazolones

Organic Letters

Volumn 16, Issue 16, 2014, Pages 4178-4181

  Zhao, Ruirui ^a   Sun, Zhongwen ^a   Mo, Mingjie ^a   Peng, Fangzhi ^a   Shao, Zhihui ^a  

^a YUNNAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ASPIDOFRACTININE; CARBAZOLE DERIVATIVE; INDOLE ALKALOID; PALLADIUM;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGENATION; STEREOISOMERISM; SYNTHESIS;

CARBAZOLES; CATALYSIS; HYDROGENATION; INDOLE ALKALOIDS; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM;

EID: 84906258511     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol501877x     Document Type: Article

References (36)

1. Richard, J. Drugs 1991, 41, 574
2. Young, J. W. Int. Appl. PCT, WO 1993000074 A1, 1993.
3. Bodhankar, S. L.; Thakurdesai, P. A.; Maurya, O. P. Pharmacologyonline 2006, 3, 153
4. Elz, S.; Heil, W. L. Bioorg. Med. Chem. Lett. 1995, 5, 667
5. Romeo, G.; Materia, L.; Pittala, V.; Modica, M.; Salerno, L.; Siracusa, M.; Russo, F.; Minneman, K. P. Bioorg. Med. Chem. 2006, 14, 5211
6. Georg, S. Expert Rev. Gastroenterol. Hepatol. 2007, 1, 15
7. van Wijngaarden, I.; Hamminga, D.; van Hes, R.; Standaar, P. J.; Tipker, J.; Tulp, M. T. M.; Mol, F.; Olivier, B.; de Jonge, A. J. Med. Chem. 1993, 36, 3693
8. Gartshore, C. J.; Lupton, D. W. Angew. Chem., Int. Ed. 2013, 52, 4113
9. Li, Z.; Zhang, S.; Wu, S.; Shen, X.; Zou, L.; Wang, F.; Li, X.; Peng, F.; Zhang, H.; Shao, Z. Angew. Chem., Int. Ed. 2013, 52, 4117
10. Mohr, J. T.; Hong, A. Y.; Stoltz, B. M. Nat. Chem. 2009, 1, 359
11. Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566
12. Eames, J.; Weerasooriya, N. Tetrahedron: Asymmetry 2001, 12, 1
13. Duhamel, L.; Duhamel, P.; Plaquevent, J.-C. Tetrahedron: Asymmetry 2004, 15, 3653
14. Yanagisawa, A.; Yamamoto, H. In Comprehensive Asymmetric Catalysis, Supplement 2; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: New York, 2004; pp 125-132.
15. Blanchet, J.; Baudoux, J.; Amere, M.; Lasne, M.-C.; Rouden, J. Eur. J. Org. Chem. 2008, 5493
16. Claraz, A.; Oudeyer, S.; Levacher, V. Curr. Org. Chem. 2012, 16, 2192
17. Nakamura, S. Org. Biomol. Chem. 2014, 12, 394
18. Oudeyer, S.; Briere, J.-F.; Levacher, V. Eur. J. Org. Chem. 2014, 10.1002/ejoc.201402213
19. Tsuji, J.; Nisar, M.; Shimizu, I. J. Org. Chem. 1985, 50, 3416
20. Mandai, T.; Imaji, M.; Takada, H.; Kawata, M.; Nokami, J.; Tsuji, J. J. Org. Chem. 1989, 54, 5395
21. Hénin, F.; Muzart, J. Tetrahedron: Asymmetry 1992, 3, 1161
22. Aboulhoda, S. J.; Hénin, F.; Muzart, J.; Thorey, C.; Behnen, W.; Martens, J.; Mehler, T. Tetrahedron: Asymmetry 1994, 5, 1321
23. Abouldoda, S. J.; Letinois, S.; Wilken, J.; Reiners, I.; Hénin, F.; Martnes, J.; Muzart, J. Tetrahedron: Asymmetry 1995, 6, 1865
24. Baur, M. A.; Riahi, A.; Hénin, F.; Muzart, J. Tetrahedron: Asymmetry 2003, 14, 2755
25. Mohr, J. T.; Nishimata, T.; Behenna, D. C.; Stoltz, B. M. J. Am. Chem. Soc. 2006, 128, 11348
26. Marinescu, S. C.; Nishimata, T.; Mohr, J. T.; Stoltz, B. M. Org. Lett. 2008, 10, 1039
27. A review on the role of vinylogy in reaction discovery: Denmark, S. E.; Heemstra, J. R., Jr.; Beutner, G. L. Angew. Chem., Int. Ed. 2005, 44, 4682
28. Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336 and references therein
29. Ban, Y.; Homna, Y.; Oishi, T. Tetrahedron Lett. 1976, 14, 1111
30. Ban, Y.; Ohnuma, T.; Oishi, T.; Kinoshita, H. Chem. Lett. 1986, 927
31. Cartier, D.; Ouahrani, M.; Lévy, J. T. Tetrahedron Lett. 1989, 30, 1951
32. Dufour, M.; Gramain, J. C.; Husson, H. P.; Sinibaldi, M. E.; Troin, Y. Tetrahedron Lett. 1989, 30, 3429
33. Wenkert, E.; Liu, S. J. Org. Chem. 1994, 59, 7677
34. Gagnon, D.; Spino, C. J. Org. Chem. 2009, 74, 6035
35. Burger, E. C.; Tunge, J. A. J. Am. Chem. Soc. 2006, 128, 10002
36. Waetzig, S. R.; Tunge, J. A. J. Am. Chem. Soc. 2007, 129, 4138