Two-step total syntheses of Canthin-6-one alkaloids: New one-pot sequential Pd-catalyzed Suzuki-Miyaura coupling and Cu-catalyzed amidation reaction

Organic Letters

Volumn 12, Issue 6, 2010, Pages 1352-1355

  Gollner, Andreas ^a,b   Koutentis, Panayiotis A ^a  

^a UNIVERSITY OF CYPRUS   (Cyprus)

^b Cyano Research Corporation Ltd   (Cyprus)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; AMIDE; CANTHIN 6 ONE; CANTHIN-6-ONE; COPPER; INDOLE DERIVATIVE; NAPHTHYRIDINE DERIVATIVE; ORGANOMETALLIC COMPOUND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; AMIDES; CATALYSIS; COPPER; INDOLES; MOLECULAR STRUCTURE; NAPHTHYRIDINES; ORGANOMETALLIC COMPOUNDS; PALLADIUM; STEREOISOMERISM;

EID: 77949794863     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100300s     Document Type: Article

References (47)

1. (a) Haynes, H. F.; Nelson, E. R.; Price, J. R. Aust .J. Res., Ser. A 1952, 5, 387.
2. (b) For a review, see: Ohmoto, T.; Koike, K. In The Alkaloids; Brossi, A., Ed.; Academic: New York, 1989; Vol. 36, p 135.
3. (a) Murakami, C.; Fukamiya, N.; Tamura, S.; Okano, M.; Bastow, K. F.; Tokuda, H.; Mukainaka, T.; Nishino, H.; Lee, K.-H. Bioorg. Med. Chem. 2004, 12, 4963.
4. (b) Thouvenel, C.; Gantier, J.-C.; Duret, P.; Fourneau, C.; Hocquemiller, R.; Ferreira, M.-E.; Rojas de Arias, A.; Fournet, A. Phytother. Res. 2003, 17, 678.
5. (c) Soriano-Agaton, F.; Lagoutte, D.; Poupon, E.; Roblot, F.; Fournet, A.; Gantier, J.-C.; Hocquemiller, R. J. Nat. Prod. 2005, 68, 1581.
6. (d) Ouyang, Y.; Koide, K.; Ohmoto, T Phytochemistry 1994, 36, 1543.
7. (e) Zapesochnaya, G. G.; Pervykh, L. N.; Kurkin, V. A. Chem. Nat. Compd. 1991, 27, 336.
8. (f) Vetrichelvan, T.; Jegadeesan, M. Ethnopharmacol. 2002, 80, 103.
9. (g) Hsieh, P.-W.; Chang, F.-R.; Lee, K.H.; Hwang, T.-L.; Chang, S.-M.; Wu, Y.-C. J. Nat. Prod 2004, 67, 1175.
10. (h) Takasu, K.; Shimogama, T.; Saiin, C.; Kim, H.-S.; Wataya, Y.; Brun, R.; Ihara, M. Chem. Pharm. Bull. 2005, 53, 653.
11. (i) O'Donnell, G.; Gibbons, S. Phytother. 2007, 21, 653.
12. (a) Kardono, L. B. S.; Angerhofer, C. K.; Tsauri, S.; Padmawmata, K.; Pemito, J. M.; Kinghorn, D. J. Nat. Prod. 1991, 54, 1360.
13. (b) Giesbrecht, A. M.; Gottlieb, H. E.; Gottlieb, O. R.; Goulart, M. O. F.; De Lama, R. A.; Santana, A. E. G. Phytochemistrv 1980, 19, 313.
14. Clarke, P. J.; Jewers, K.; Jones, H. F. J. Chem. Soc., Perkin Trans. I , 1980, 1614.
15. Bröckelmann, M. G.; Dasenbrock, J.; Steffan, B.; Steglich, W.; Wang, Y.; Raabe, G.; Fleischhauer, J. Eur. J. Org. Chem. 2004, 30, 4856.
16. (a) Cain, M.; Campos, O.; Guzman, F.; Cook, J. M. J. Am. Chem. Soc. 1983, 105, 907.
17. (b) Hagen, T. J.; Cook, J. M. Tetrahedron Lett. 1988, 29, 2421.
18. (c) Hagen, T. J.; Narayanan, K.; Names, J.; Cook, M. J. Org. Chem. 1989, 54, 2170.
19. (d) Benson, S. C.; Li, J. H.; Snyder, J. K. J. Org. Chem. 1992, 57, 5285.
20. (e) Li, J.-H.; Snyder, J. K. Tetrahedron Lett. 1994, 35, 1485.
21. (f) Maarseveen, J. H. V.; Mulders, S. J. E.; Aben, R. W. M.; Kruse, C. G.; Scheeren, H. W. Tetrahedron 1995, 51, 4841.
22. (g) Markgraf, J. H.; Finkelstein, M.; Cort, J. R. Tetrahedron 1996, 52, 461.
23. (h) Markgraf, J. H.; Snyder, S. A.; Vosburg, D. A. Tetrahedron Lett. 1998, 39, 1111.
24. (i) Rossler, U.; Blechert, S.; Steckhan, E. Tetrahedron Lett. 1999, 40, 7075.
25. (j) Snyder, S. A.; Vosburg, D. A.; Jarvis, M. G.; Markgraf, J. H. Tetrahedron. 2000, 56, 5329.
26. (k) Lindsley, C. W.; Wisnoski, D. D.; Wang, Y.; Leister, W. H.; Zhao, Z. Tetrahedron. Lett. 2003, 44, 4495.
27. (l) Czerwinski, K. M.; Zificsak, C. A.; Stevens, J.; Oberbeck, M.; Randlett, C.; King, M.; Mennen, S. Synth. Commun. 2003, 33, 1225.
28. (m) Condie, G. C.; Bergman, J. Eur. J. Org. Chem. 2004, 30, 1286.
29. (n) Condie, G. C.; Bergman, J. J. Heterocycl. Chem. 2004, 41, 531.
30. (o) Suzuki, H.; Abi, M.; Ebihara, Y.; Gyoutoko, H.; Furuya, H.; Murakami, Y.; Okuno, H. Synthesis 2005, 28.
31. (p) Nourry, A.; Legoupy, S.; Huet, F. Tetrahedron Lett. 2007, 48, 6014.
32. (q) Singh, V.; Hutait, S.; Batra, S. Eur. J. Org. Chem. 2009, 35, 6211.
33. (a) Morgentin, R.; Pasquet, G.; Boutron, P.; .Tung, F.; Lamorlette, M.; Maudet, M.; Ple, P. Tetrahedron 2008, 64, 2772.
34. (b) AlemparteGallardo, C.; Ballell-Pages, L.; Barros-Aguirre, D.; Cacho-Izquierdo, M.; Castro-Pichel, J.; Fiandor-Roman, J. M.; Hennessy, A. J.; Pearson, N. D.; Remuinan-Blanco, M. J. WO2009090222, 2009.
35. Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421.
36. Seventy-seven substituted 2-chlorophenylboronic acids are comercially available (SciFinder 11 January, 2010).
37. For recent examples, see: (a) Candito, D. A.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 6713.
38. (b) Fayol, A.; Fang, Y.-Q.; Lautens, M. Org. Lett. 2006, 8, 4203.
39. (c) Fang, Y.-Q.; Lautens, M. Org. Lett. 2005, 7, 3449.
40. (d) Furuta, T.; Kitamura, Y.; Hahimoto, A.; Fujii, S.; Tanaka, K.; Kan, T. Org. Lett. 2007, 9, 183.
41. (e) Kitamura, Y.; Yashikawa, S.; Furuta, T.; Kan, T. Synlett 2008, 377.
42. (f) Ferraccioli, R.; Carenzi, D.; Motti, E.; Catellani, M. J. Am. Chem. Soc. 2006, 128, 722.
43. (g) Ferraccioli, R.; Carenzi, D.; Rombolà, O.; Catellani, M. Org. Lett. 2004, 6, 4759.
44. (a) Loones, K. T. J.; Maes, B. U. W.; Meyers, C.; Deruytter, J. J. Org. Chem. 2006, 71, 260.
45. (b) Collot, V.; Bovy, R.; Rault, S. Tetrahedron. Lett, 2000, 41, 9053.
46. (c) Lira, R.; Wolfe, J. P. J. Am. Chem. Soc. 2004, 126, 13906.
47. The simultaneous addition of both the Pd and Cu catalysts at the start of the reaction gave mainly recovered naphthyridone 6. More information can be found in the Supporting Information.