Synthesis of pyrrolo-isoquinolines related to the lamellarins using silver-catalyzed cycloisomerization/dipolar cycloaddition

Journal of the American Chemical Society

Volumn 129, Issue 25, 2007, Pages 7744-7745

  Su, Shun ^a   Porco Jr , John A ^a  

^a Boston University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ISOQUINOLINE DERIVATIVE; PYRROLE DERIVATIVE; SILVER;

ARTICLE; CATALYST; CYCLIZATION; CYCLOADDITION; DIPOLE; ISOMERIZATION; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

CATALYSIS; ISOQUINOLINES; MOLECULAR STRUCTURE; PYRROLES; SILVER SULFADIAZINE;

EID: 34347271241     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja072737v     Document Type: Article

References (32)

1. Bailly, C. Curr. Med. Chem. Anti-Cancer Agents 2004, 4, 363.
2. Marco, E.; Laine, W.; Tardy, C.; Lansiaux, A.; Iwao, M.; Ishibashi, F.; Bailly, C.; Gago, F. J. Med. Chem. 2005, 48, 3796.
3. Kluza, J.; Gallego, M.-A.; Loyens, A.; Beauvillain, J-C.; Fernandez, Sousa-Faro, J-M.; Cuevas, C.; Marchetti, P.; Bailly, C. Cancer Res. 2006, 66, 3177.
4. Reddy, M. V. R.; Rao, M. R.; Rhodes, D.; Hansen, M. S. T.; Rubins, K.; Bushman, F. D.; Venkateswarlu, Y.; Faulkner, D. J. J. Med. Chem. 1999, 42, 1901.
5. Aubry, A.; Pan, X-S.; Fisher, L. M.; Jarlier, V.; Cambau, E. Antimicro. Agents Chemother. 2004, 48, 1281.
6. For the synthesis of pyrrolo-isoquinolines, see: (a) Seregin, I. V.; Gevorgyan, V. J. Am. Chem. Soc. 2006, 128, 12050.
7. (b) Yavari, I.; Sabbaghan, M.; Hossaini, Z. Syn. Lett. 2006, 2501.
8. (c) Kobayashi, M.; Tanabe, M.; Kondo, K.; Aoyama, T. Tetrahedron Lett. 2006, 47, 1469.
9. Synthetic studies: (a) Banwell, M.; Flynn, B.; Hockless, D. Chem. Commun. 1997, 2259.
10. (b) Handy, S. T.; Zhang, Y.; Bregman, H. J. Org. Chem. 2004, 69, 2346.
11. (c) Handy, S. T.; Zhang, Y. Org. Prep. Proc. Int. 2005, 37, 411.
12. (d) Pla, D.; Marchal, A.; Olsen, C. A.; Albericio, F.; Alvarez, M. J. Org. Chem. 2005, 70, 8231.
13. (e) Ploypradith, P.; Petchmanee, T.; Sahakitpichan, P.; Litvinas, N. D.; Ruchirawat, S. J. Org. Chem. 2006, 71, 9440.
14. (a) Huang, Q.; Larock, R. C. J. Org. Chem. 2003, 68, 980.
15. (b) Dai, G.; Larock, R. C. J. Org. Chem. 2003, 68, 920.
16. (c) Rubin, M.; Sromek, A. W.; Gevorgyan, V. Syn. Lett. 2003, 2265.
17. (d) Ohtaka, M.; Nakamura, H.; Yamamoto, Y. Tetrahedron Lett. 2004, 45, 7339.
18. (e) Asao, N.; Yudha, S.; Nogami, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2005, 44, 5526.
19. (f) Yanada, R.; Obika, S.; Kono, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2006, 45, 3822.
20. For metal-mediated azomethine ylide formation/dipolar cycloaddition, see: (a) Padwa, A.; Dean, D. C.; Zhi, L. J. Am. Chem. Soc. 1992, 114, 593.
21. For recent reviews on azomethine ylide cycloaddition, see: (b) Najera, C.; Sansano, J. M. Curr. Org. Chem. 2003, 7, 1105.
22. (c) Coldham, I.; Hufton, R. Chem. Rev. 2005, 105, 2765.
23. For cycloadditions of metal-containing azomethine ylides from alkynyl imines, see: (d) Kusama, H.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 11592.
24. (e) Takaya, J.; Kusama, H.; Iwasawa, N. Chem. Lett. 2004, 33, 16.
25. Beeler, A. B.; Su, S.; Singleton, C. A.; Porco, J. A., Jr. J. Am. Chem. Soc. 2007, 129, 1413.
26. See Supporting Information for complete experimental details.
27. Asao, N.; Iso, K.; Yudha, S. Org. Lett. 2006, 8, 4149.
28. See for example: Suga, H.; Inoue, K.; Inoue, S.; Kakehi, A. J. Am. Chem. Soc. 2002, 124, 14836.
29. Matsumoto, K.; Uchida, T.; Konishi, H.; Watanabe, Y.; Aoyama, K.; Asahi, M. Chem. Lett. 1987, 807.
30. For dihydropyrroles resembling compound 41, see: Bacu, E.; Samson-Belei, D.; Nowogrocki, G.; Couture, A.; Grandclaudon, P. Org. Biomol. Chem. 2003, 1, 2377.
31. (a) Cuadro, A. M.; Alvarez-Builla, J.; Vaquero, J. J. Heterocycles 1989, 29, 57.
32. (b) Gandasegui, M. T.; Alvarez-Builla, J.; Florencio, F. Heterocycles 1994, 37, 174.