Total synthesis of calothrixin A and B via C-H activation

Journal of Organic Chemistry

Volumn 78, Issue 6, 2013, Pages 2802-2807

  Ramkumar, Nagarajan ^a   Nagarajan, Rajagopal ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

C-H ACTIVATION; CROSS COUPLING REACTIONS; PHENANTHRIDINE ALKALOIDS; TOTAL SYNTHESIS;

CHEMISTRY; ORGANIC COMPOUNDS;

ACTIVATION ANALYSIS;

ALKALOID DERIVATIVE; CALOTHRIXIN A; CALOTHRIXIN B; CARBAZOLE DERIVATIVE; CARBON; HYDROGEN; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; COVALENT BOND; CROSS COUPLING REACTION; DEMETHYLATION; SYNTHESIS;

ALKALOIDS; CARBAZOLES; CATALYSIS; HYDROGEN BONDING; INDOLE ALKALOIDS; MOLECULAR STRUCTURE; PALLADIUM; PHENANTHRIDINES;

EID: 84875202074     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302821v     Document Type: Article

References (50)

1. Rickards, R. W.; Rothschild, J. M.; Willis, A. C.; de Chazal, N. M.; Kirk, J.; Kirk, K.; Saliba, K. J.; Smith, G. D. Tetrahedron 1999, 55, 13513-13520
2. Matsumoto, K.; Choshi, T.; Hourai, M.; Zamami, Y.; Sasaki, K.; Abe, T.; Ishikura, M.; Hatae, N.; Iwamura, N.; Tohyama, S.; Nobuhiro, J.; Hibino, S. Bioorg. Med. Chem. Lett. 2012, 22, 4762-4764
3. Bernardo, P. H.; Chai, C. L. L.; Heath, G. A.; Mahon, P. J.; Smith, G. D.; Waring, P.; Wilkes, B. A. J. Med. Chem. 2004, 47, 4958-4963
4. Khan, Q. A.; Lu, J.; Hecht, S. M. J. Nat. Prod. 2009, 72, 438-442
5. Kelly, T. R.; Zhao, Y.; Cavero, M.; Torneiro, M. Org. Lett. 2000, 2, 3735-3737
6. Choshi, T.; Hibino, S. Heterocycles 2009, 77, 85-97
7. Tohyama, S.; Choshi, T.; Matsumoto, K.; Yamabuki, A.; Hieda, Y.; Nobuhiro, J.; Hibino, S. Heterocycles 2010, 82, 397-416
8. Abe, T.; Ikeda, T.; Yanada, R.; Ishikura, M. Org. Lett. 2011, 13, 3356-3359
9. Bhosale, S. M.; Gawade, R. L.; Puranik, V. G.; Kusurkar, R. S. Tetrahedron Lett. 2012, 53, 2894-2896
10. Bennasar, M. -L.; Roca, T.; Ferrando, F. Org. Lett. 2006, 8, 561-564
11. Bernardo, P. H.; Chai, C. L. L. J. Org. Chem. 2003, 68, 8906-8909
12. Bernardo, P. H.; Chai, C. L. L.; Elix, J. A. Tetrahedron Lett. 2002, 43, 2939-2940
13. Sissouma, D.; Maingot, L.; Collet, S.; Guingant, A. J. Org. Chem. 2006, 71, 8384-8389
14. Tohyama, S.; Choshi, T.; Matsumoto, K.; Yamabuki, A.; Ikegata, K.; Nobuhiro, J.; Hibino, S. Tetrahedron Lett. 2005, 46, 5263-5264
15. McErlean, C. S. P.; Sperry, J.; Blake, A. J.; Moody, C. J. Tetrahedron 2007, 63, 10963-10970
16. Yamabuki, A.; Fujinawa, H.; Choshi, T.; Tohyama, S.; Matsumoto, K.; Ohnuma, K.; Nobuhiro, J.; Hibino, S. Tetrahedron Lett. 2006, 47, 5859-5861
17. Sperry, J.; McErlean, C. S. P.; Slawin, A. M. Z.; Moody, C. J. Tetrahedron Lett. 2007, 48, 231-234
18. Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; deMeijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.
19. Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley Interscience: New York, 2002.
20. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147-1169
21. Díaz-Requejo, M. M.; Pérez, P. J. Chem. Rev. 2008, 108, 3379-3394
22. Schmidt, A. W.; Reddy, K. R.; Knölker, H.-J. Chem. Rev. 2012, 112, 3193-3328
23. Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731-1770
24. Díaz-Requejo, M. M.; Pérez, P. J. Chem. Rev. 2008, 108, 3379-3394
25. Knölker, H.-J. Chem. Lett. 2009, 38, 8-13
26. Knölker, H.-J.; Reddy, K. R. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: Amsterdam, 2008; Vol. 65, p 1.
27. Bauer, I.; Knölker, H.-J. Top. Curr. Chem. 2012, 309, 203-253
28. Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1469
29. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442-4489
30. Pulido, F. J.; Barbero, A.; García, C. Tetrahedron 2009, 65, 5535-5540
31. Bowie, A. L.; Trauner, D. J. Org. Chem. 2009, 74, 1581-1586
32. Frye, E. C.; O'Connor, C. J.; Twigg, D. G.; Elbert, B.; Laraia, L.; Hulcoop, D. G.; Venkitaraman, A. R.; Spring, D. R. Chem.-Eur. J. 2012, 18, 8774-8779
33. Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417-1492
34. Weibel, J.-M.; Blanc, A.; Pale, P. Chem. Rev. 2008, 108, 3149-3173
35. Shi, W.; Liu, C.; Lei, A. Chem. Soc. Rev. 2011, 40, 2761-2776
36. Harayama, T.; Akamatsu, H.; Okamura, K.; Miyagoe, T.; Akiyama, T.; Abe, H.; Takeuchi, Y. J. Chem. Soc., Perkin Trans. 1 2001, 523-528
37. Olah, G. A; Narang, S. C. Tetrahedron 1982, 38, 2225-2227
38. Ho, T.-L.; Olah, G. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 774-775
39. Ho, T.-L.; Olah, G. A. Synthesis 1977, 417-418
40. Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004, 104, 6217-6254
41. Möoller, K.; Wienhöofer, G.; Schröoder, K.; Join, B.; Junge, K.; Beller, M. Chem.-Eur. J. 2010, 16, 10300-10303
42. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293-1314
43. Asche, C.; Frank, W.; Albert, A.; Kucklaender, U. Bioorg. Med. Chem. 2005, 13, 819-837
44. Tao, Z.-F.; Sowin, T. J.; Lin, N.-H. Tetrahedron Lett. 2005, 46, 7615-7618
45. Katritzky, A. R.; Lagowski, J. M. Chemistry of the Heterocyclic N-Oxides; Academic Press: London, 1971.
46. Rousseau, R. J.; Robins, R. K. J. Heterocycl. Chem. 1965, 2, 196-201
47. Katritzky, A. R.; Lam, J. N. Heterocycles 1992, 33, 1011-1049
48. Hanada, S.; Tsutsumi, E.; Motoyama, Y.; H. Nagashima, H. J. Am. Chem. Soc. 2009, 131, 15032-15040
49. Das, S.; Addis, D.; Zhou, S.; Junge, K.; Beller, M. J. Am. Chem. Soc. 2010, 132, 1770-1771
50. Pelletier, G.; Bechara, W. S.; Charette, A. B. J. Am. Chem. Soc. 2010, 132, 12817-12819