Copper-catalyzed cyclization of lodo-tryptophans: A straightforward synthesis of pyrroloindoles

Organic Letters

Volumn 10, Issue 17, 2008, Pages 3841-3844

  Coste, Alexis ^a   Toumi, Mathieu ^a   Wright, Karen ^a   Razafimahaléo, Vanessa ^a   Couty, François ^a   Marrot, Jérome ^a   Evano, Gwilherm ^a  

^a UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; DIPEPTIDE; DRUG DERIVATIVE; INDOLE ALKALOID; INDOLE DERIVATIVE; IODINATED HYDROCARBON; PYRROLE DERIVATIVE; TRYPTOPHAN;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; COPPER; CYCLIZATION; DIPEPTIDES; HYDROCARBONS, IODINATED; INDOLE ALKALOIDS; INDOLES; PYRROLES; STEREOISOMERISM; TRYPTOPHAN;

EID: 55949121639     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8015513     Document Type: Article

References (36)

1. For reviews, see: (a) Crich, D.; Banerjee, A. Acc. Chem. Res. 2007, 40, 151.
2. (b) Schmidt, M. A.; Movassaghi, M. Synlett 2008, 313.
3. Takase, S.; Iwami, M.; Ando, T.; Okamoto, M.; Yoshida, K.; Horiai, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiot. 1984, 37, 1320.
4. Hayashi, H.; Fujiwara, T.; Murao, S.; Arai, M. Agric. Biol. Chem. 1991, 55, 3143.
5. Pettit, G. R.; Tan, R.; Herald, D. L.; Cerny, R. L.; Williams, M. D. J. Org. Chem. 1994, 59, 1593.
6. Massiot, G.; Thépenier, P.; Jacquier, M.-J.; Le Men-Olivier, L.; Delaude, C. Heterocydes 1989, 29, 1435.
7. Takayama, H.; Mori, I.; Kitajima, M.; Aimi, N.; Lajis, N. H. Org. Lett. 2004, 6, 2945.
8. For selected syntheses, see: (a) Depew, K. M.; Marsden, S. P.; Zatorska, D.; Zatorski, A.; Bornmann, W. G.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 11953.
9. (b) Roe, J. M.; Webster, R. A. B.; Ganesan, A. Org. Lett. 2003, 3, 2825.
10. (c) Baran, P. S.; Guerrero, C. A.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 5628.
11. (d) Hewitt, P. R.; Cleator, E.; Ley, S. V. Org. Biomol. Chem. 2004, 2, 2415.
12. (e) Lindel, T.; Bräuchle, L.; Golz, G.; Böhrer, P. Org. Lett. 2007, 9, 283.
13. (f) Movassaghi, M.; Schmidt, M. A.; Ashenhurst, J. A. Angew. Chem., Int. Ed. 2008, 47, 1485.
14. (g) Shangguan, N.; Hehre, W. J.; Ohlinger, W. S.; Beavers, M. P.; Joullié, M. J. Am. Chem. Soc. 2008, 130, 6281.
15. (h) Dounay, A. B.; Humphreys, P. G.; Overman, L. E.; Wrobleski, A. D. J. Am. Chem. Soc. 2008, 130, 5368.
16. (i) Matsuda, Y.; Kitajima, M.; Takayama, H. Org. Lett. 2008, 10, 125.
17. For examples, see: (a) Ohno, M.; Tanaka, S.; Shieh, T.-C.; Spande, T. F. J. Org. Chem. 1984, 49, 5069.
18. (b) Kamenecka, T. M.; Danishefsky, S. J. Chem. Eur. J. 2001, 7, 41.
19. (c) Okada, M.; Sato, I.; Cho, S. J.; Dubnau, D.; Sakagami, Y. Tetrahedron 2006, 62, 8907.
20. (d) Cardoso, A. S.; Marques, M. M. B.; Srinivasan, N.; Prabhakar, S.; Lobo. A. M. Tetrahedron 2007, 63, 10211.
21. (a) Ohno, M.; Spande, T. F.; Witkop, B. J. Am. Chem. Soc. 1968, 90, 6521.
22. (b) Ohno, M.; Spande, T. F.; Witkop, B. J. Am. Chem. Soc. 1970, 92, 343.
23. Bailey, P. D.; Cochrane, P. J.; Irvine, F.; Morgan, K. M.; Pearson, D. P. J.; Veal, K. T. Tetrahedron Lett. 1999, 40, 4593.
24. (a) Toumi, M.; Couty, F.; Evano, G. Angew. Chem., Int. Ed. 2007, 46, 572.
25. (b) Toumi, M.; Couty, F.; Evano, G. J. Org. Chem. 2007, 72, 9003.
26. (c) Toumi, M.; Couty, F.; Evano, G. Synlett 2008, 29.
27. (a) Mingoia, Q. Gazz. Chim. Ital. 1930, 60, 509.
28. (b) Snider, B. B.; Zeng, H. J. Org. Chem. 2003, 68, 545.
29. (a) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727.
30. (b) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421.
31. Yuen, J.; Fang, Y.-Q.; Lautens, M. Org. Lett. 2006, 8, 653.
32. For an ortho effect with trifluoroacetamides, see: (a) Cai, Q.; Zou, B.; Ma, D. Angew. Chem., Int. Ed. 2006, 45, 1276.
33. (b) Xie, X.; Chen, Y.; Ma, D. J. Am. Chem. Soc. 2006, 128, 16050.
34. (c) Zou, B.; Yuan, Q.; Ma, D. Angew. Chem., Int. Ed. 2007, 46, 2598.
35. (d) Liu, F.; Ma, D. J. Org. Chem. 2007, 72, 4844.
36. 1H NMR analysis of crude reaction mixtures.