Directed ortho metalation approach to C-7-substituted indoles. Suzuki-Miyaura cross coupling and the synthesis of pyrrolophenanthridone alkaloids

Organic Letters

Volumn 5, Issue 11, 2003, Pages 1899-1902

  Hartung, Christian G ^a   Fecher, Anja ^a   Chapell, Brian ^a,b   Snieckus, Victor ^a  

^a QUEEN S UNIVERSITY   (Canada)

^b Mohawk College of Applied Arts and Technology   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; INDOLE DERIVATIVE; PHENANTHRIDINE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; COUPLING FACTOR; CROSS LINKING; DEPROTECTION REACTION; METALATION; QUANTUM YIELD; SILYLATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0141741411     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0344772     Document Type: Article

References (48)

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8. For a selection of de novo methods of indole ring construction, see: (a) Batcho, A. D.; Leimgruber, W. Org. Synth. 1985, 63, 214. (b) Bartoli, G.; Bosco, M.; Dalpozzo, R.; Palmieri, G.; Marcantoni, E. J. Chem. Soc., Perkin Trans. 1 1991, 2757. (c) Soederberg, B. C.; Shriver, J. A. J. Org. Chem. 1997, 62, 5838, and refs cited therein. (d) Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045 and refs cited therein. (e) Beller, M.; Breindl, C.; Riermeier, T. H.; Tillack, A. J. Org. Chem. 2001, 66, 1403. (f) Lindsay, D. M.; Dohle, W.; Jensen, A. E.; Kopp, F.; Knochel, P. Org. Lett. 2002, 4, 1819.
9. For a selection of de novo methods of indole ring construction, see: (a) Batcho, A. D.; Leimgruber, W. Org. Synth. 1985, 63, 214. (b) Bartoli, G.; Bosco, M.; Dalpozzo, R.; Palmieri, G.; Marcantoni, E. J. Chem. Soc., Perkin Trans. 1 1991, 2757. (c) Soederberg, B. C.; Shriver, J. A. J. Org. Chem. 1997, 62, 5838, and refs cited therein. (d) Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045 and refs cited therein. (e) Beller, M.; Breindl, C.; Riermeier, T. H.; Tillack, A. J. Org. Chem. 2001, 66, 1403. (f) Lindsay, D. M.; Dohle, W.; Jensen, A. E.; Kopp, F.; Knochel, P. Org. Lett. 2002, 4, 1819.
10. For a selection of de novo methods of indole ring construction, see: (a) Batcho, A. D.; Leimgruber, W. Org. Synth. 1985, 63, 214. (b) Bartoli, G.; Bosco, M.; Dalpozzo, R.; Palmieri, G.; Marcantoni, E. J. Chem. Soc., Perkin Trans. 1 1991, 2757. (c) Soederberg, B. C.; Shriver, J. A. J. Org. Chem. 1997, 62, 5838, and refs cited therein. (d) Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045 and refs cited therein. (e) Beller, M.; Breindl, C.; Riermeier, T. H.; Tillack, A. J. Org. Chem. 2001, 66, 1403. (f) Lindsay, D. M.; Dohle, W.; Jensen, A. E.; Kopp, F.; Knochel, P. Org. Lett. 2002, 4, 1819.
11. (a) Gribble, G. W. In Advances in Heterocyclic Natural Product Synthesis; Pearson, W. H., Ed.; Jai Press: Greenwich, CT, 1990; Vol. 1, p 43.
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15. For relevant selected indole metalation chemistry, see: (d) Comins, D. L. Synlett 1992, 615. (e) Matsuzono, M.; Fukuda, T.; Iwao, M. Tetrahedron Lett. 2001, 42, 7621. (f) Vasquez, E.; Davies, I. W.; Payack, J. F. J. Org. Chem. 2002, 67, 7551.
16. For relevant selected indole metalation chemistry, see: (d) Comins, D. L. Synlett 1992, 615. (e) Matsuzono, M.; Fukuda, T.; Iwao, M. Tetrahedron Lett. 2001, 42, 7621. (f) Vasquez, E.; Davies, I. W.; Payack, J. F. J. Org. Chem. 2002, 67, 7551.
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20. (b) Chauder, B.; Larkin, A.; Snieckus, V. Org. Lett. 2002, 4, 815.
21. For C-4/C-6 DoM chemistry on C-5 O-carbamates, see: (c) Griffen, E. J.; Roe, D. G.; Snieckus, V. J. Org. Chem. 1995, 60, 1484.
22. Iwao, M.; Kuraishi, T. Heterocycles 1992, 34, 1031.
23. Fukuda, T.; Maeda, R.; Iwao, M. Tetrahedron 1999, 55, 9151.
24. 3 derivatives, see: (a) Masters, N. F.; Mathews, N.; Nechvatal, G.; Widdowson, D. A. Tetrahedron 1989, 45, 5955. Via C-H activation, see: (b) Chatani, N.; Yorimitsu, S.; Asaumi, T.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2002, 67, 7557.
25. 3 derivatives, see: (a) Masters, N. F.; Mathews, N.; Nechvatal, G.; Widdowson, D. A. Tetrahedron 1989, 45, 5955. Via C-H activation, see: (b) Chatani, N.; Yorimitsu, S.; Asaumi, T.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2002, 67, 7557.
26. For use of DEB-indole for C-2 and C-3 functionalization by metalation reactions, see: Fukuda, T.; Mine, Y.; Iwao, M. Tetrahedron 2001, 57, 975.
27. Mills, R. J.; Taylor, N. J.; Snieckus, V. J. Org. Chem. 1989, 54, 4372.
28. Achenbach, H.; Renner, C. Heterocycles 1985, 23, 2075.
29. Grundon, M. F. Nat. Prod. Rep. 1989, 6, 79.
30. Jones, R. A. Inflammopharmacology 2001, 9, 63.
31. Gray, M.; Chapell, B. J.; Felding, J.; Taylor, N. J.; Snieckus, V. Synlett 1998, 422.
32. For the complete study, see: Chapell, B. J., Ph.D. Thesis, University of Waterloo, Waterloo, ON, Canada, 2001.
33. This may be reasonably rationalized by a complex induced proximity effect (CIPE): Beak, P.; Meyers, A. I. Acc. Chem. Res. 1986, 19, 356.
34. Success of this reaction is highly dependent on the quality and quantity of the s-BuLi; see also footnote 23 in ref 8.
35. For entries 6 and 11, products 9 (10%) and 10 (16%) were isolated; for entries 9 and 10, 11 (10-20%) was obtained. Product 11, presumably the result of benzyne formation of the normal product (7h, 7i) followed by carbamoyl α-deprotonation-cyclization, is formed in 50% yield under the following conditions: (1) 3 equiv of s-BuLi/TMEDA/THF/-78°C/2 h; (2) 3 equiv of Br2 or I2/-78°C → rt (Supporting Information).
36. Comins, D. L.; Stroud, E. D. Tetrahedron Lett. 1986, 27, 1869.
37. (b) Castells, J.; Troin, Y.; Diez, A.; Rubiralta, M.; Grierson, D. S.; Husson, H. P. Tetrahedron 1991, 47, 7911.
38. Considering the explosion of cross-coupling chemistry, it is fair to say that indole C-7 derivatives have been infrequently described: see, e.g.: (a) Siddiqui, M. A.; Snieckus, V. Tetrahedron Lett. 1990, 31, 1523. (b) Sakamoto, T.; Yasukura, A.; Kondo, Y.; Yakamaka, H. Heterocycles 1993, 36, 2597. (c) Black, D. S. C.; Keller, P. A.; Kumar, N. Tetrahedron 1993, 49, 151. (d) Banwell, M. G.; Bissett, B. D.; Busato, S.; Cowden, C. J.; Hockeless, D. C. R.; Holman, J. W.; Read, R. W.; Wu, A. W. J. Chem. Soc., Chem. Commun. 1995, 2551. (e) Hutchings, R. H.; Meyers, A. I. J. Org. Chem. 1996, 61, 1004. (f) Carbonnelle, A.-C.; Zamora, E. G.; Beugelmans, R.; Rossi, G. Tetrahedron Lett. 1998, 39, 4467 and refs cited therein. (g) Tsuge, O.; Hatta, T.; Tsuchiyama, H. Chem. Lett. 1998, 155.
39. Considering the explosion of cross-coupling chemistry, it is fair to say that indole C-7 derivatives have been infrequently described: see, e.g.: (a) Siddiqui, M. A.; Snieckus, V. Tetrahedron Lett. 1990, 31, 1523. (b) Sakamoto, T.; Yasukura, A.; Kondo, Y.; Yakamaka, H. Heterocycles 1993, 36, 2597. (c) Black, D. S. C.; Keller, P. A.; Kumar, N. Tetrahedron 1993, 49, 151. (d) Banwell, M. G.; Bissett, B. D.; Busato, S.; Cowden, C. J.; Hockeless, D. C. R.; Holman, J. W.; Read, R. W.; Wu, A. W. J. Chem. Soc., Chem. Commun. 1995, 2551. (e) Hutchings, R. H.; Meyers, A. I. J. Org. Chem. 1996, 61, 1004. (f) Carbonnelle, A.-C.; Zamora, E. G.; Beugelmans, R.; Rossi, G. Tetrahedron Lett. 1998, 39, 4467 and refs cited therein. (g) Tsuge, O.; Hatta, T.; Tsuchiyama, H. Chem. Lett. 1998, 155.
40. Considering the explosion of cross-coupling chemistry, it is fair to say that indole C-7 derivatives have been infrequently described: see, e.g.: (a) Siddiqui, M. A.; Snieckus, V. Tetrahedron Lett. 1990, 31, 1523. (b) Sakamoto, T.; Yasukura, A.; Kondo, Y.; Yakamaka, H. Heterocycles 1993, 36, 2597. (c) Black, D. S. C.; Keller, P. A.; Kumar, N. Tetrahedron 1993, 49, 151. (d) Banwell, M. G.; Bissett, B. D.; Busato, S.; Cowden, C. J.; Hockeless, D. C. R.; Holman, J. W.; Read, R. W.; Wu, A. W. J. Chem. Soc., Chem. Commun. 1995, 2551. (e) Hutchings, R. H.; Meyers, A. I. J. Org. Chem. 1996, 61, 1004. (f) Carbonnelle, A.-C.; Zamora, E. G.; Beugelmans, R.; Rossi, G. Tetrahedron Lett. 1998, 39, 4467 and refs cited therein. (g) Tsuge, O.; Hatta, T.; Tsuchiyama, H. Chem. Lett. 1998, 155.
41. Considering the explosion of cross-coupling chemistry, it is fair to say that indole C-7 derivatives have been infrequently described: see, e.g.: (a) Siddiqui, M. A.; Snieckus, V. Tetrahedron Lett. 1990, 31, 1523. (b) Sakamoto, T.; Yasukura, A.; Kondo, Y.; Yakamaka, H. Heterocycles 1993, 36, 2597. (c) Black, D. S. C.; Keller, P. A.; Kumar, N. Tetrahedron 1993, 49, 151. (d) Banwell, M. G.; Bissett, B. D.; Busato, S.; Cowden, C. J.; Hockeless, D. C. R.; Holman, J. W.; Read, R. W.; Wu, A. W. J. Chem. Soc., Chem. Commun. 1995, 2551. (e) Hutchings, R. H.; Meyers, A. I. J. Org. Chem. 1996, 61, 1004. (f) Carbonnelle, A.-C.; Zamora, E. G.; Beugelmans, R.; Rossi, G. Tetrahedron Lett. 1998, 39, 4467 and refs cited therein. (g) Tsuge, O.; Hatta, T.; Tsuchiyama, H. Chem. Lett. 1998, 155.
42. Considering the explosion of cross-coupling chemistry, it is fair to say that indole C-7 derivatives have been infrequently described: see, e.g.: (a) Siddiqui, M. A.; Snieckus, V. Tetrahedron Lett. 1990, 31, 1523. (b) Sakamoto, T.; Yasukura, A.; Kondo, Y.; Yakamaka, H. Heterocycles 1993, 36, 2597. (c) Black, D. S. C.; Keller, P. A.; Kumar, N. Tetrahedron 1993, 49, 151. (d) Banwell, M. G.; Bissett, B. D.; Busato, S.; Cowden, C. J.; Hockeless, D. C. R.; Holman, J. W.; Read, R. W.; Wu, A. W. J. Chem. Soc., Chem. Commun. 1995, 2551. (e) Hutchings, R. H.; Meyers, A. I. J. Org. Chem. 1996, 61, 1004. (f) Carbonnelle, A.-C.; Zamora, E. G.; Beugelmans, R.; Rossi, G. Tetrahedron Lett. 1998, 39, 4467 and refs cited therein. (g) Tsuge, O.; Hatta, T.; Tsuchiyama, H. Chem. Lett. 1998, 155.
43. Considering the explosion of cross-coupling chemistry, it is fair to say that indole C-7 derivatives have been infrequently described: see, e.g.: (a) Siddiqui, M. A.; Snieckus, V. Tetrahedron Lett. 1990, 31, 1523. (b) Sakamoto, T.; Yasukura, A.; Kondo, Y.; Yakamaka, H. Heterocycles 1993, 36, 2597. (c) Black, D. S. C.; Keller, P. A.; Kumar, N. Tetrahedron 1993, 49, 151. (d) Banwell, M. G.; Bissett, B. D.; Busato, S.; Cowden, C. J.; Hockeless, D. C. R.; Holman, J. W.; Read, R. W.; Wu, A. W. J. Chem. Soc., Chem. Commun. 1995, 2551. (e) Hutchings, R. H.; Meyers, A. I. J. Org. Chem. 1996, 61, 1004. (f) Carbonnelle, A.-C.; Zamora, E. G.; Beugelmans, R.; Rossi, G. Tetrahedron Lett. 1998, 39, 4467 and refs cited therein. (g) Tsuge, O.; Hatta, T.; Tsuchiyama, H. Chem. Lett. 1998, 155.
44. Considering the explosion of cross-coupling chemistry, it is fair to say that indole C-7 derivatives have been infrequently described: see, e.g.: (a) Siddiqui, M. A.; Snieckus, V. Tetrahedron Lett. 1990, 31, 1523. (b) Sakamoto, T.; Yasukura, A.; Kondo, Y.; Yakamaka, H. Heterocycles 1993, 36, 2597. (c) Black, D. S. C.; Keller, P. A.; Kumar, N. Tetrahedron 1993, 49, 151. (d) Banwell, M. G.; Bissett, B. D.; Busato, S.; Cowden, C. J.; Hockeless, D. C. R.; Holman, J. W.; Read, R. W.; Wu, A. W. J. Chem. Soc., Chem. Commun. 1995, 2551. (e) Hutchings, R. H.; Meyers, A. I. J. Org. Chem. 1996, 61, 1004. (f) Carbonnelle, A.-C.; Zamora, E. G.; Beugelmans, R.; Rossi, G. Tetrahedron Lett. 1998, 39, 4467 and refs cited therein. (g) Tsuge, O.; Hatta, T.; Tsuchiyama, H. Chem. Lett. 1998, 155.
45. For previous syntheses, see: (a) ref 21 and refs cited therein. (b) Miki, Y.; Shirokoshi, H.; Matsushita, K.-i. Tetrahedron Lett. 1999, 40, 4347 and refs cited therein. (c) Boger, D. L.; Wolkenberg, S. E. J. Org. Chem. 2000, 65, 9120 and refs cited therein. (d) Pouysegu, L.; Avellan, A.-V.; Quideau, S. J. Org. Chem. 2002, 67, 3425 and refs cited therein.
46. For previous syntheses, see: (a) ref 21 and refs cited therein. (b) Miki, Y.; Shirokoshi, H.; Matsushita, K.-i. Tetrahedron Lett. 1999, 40, 4347 and refs cited therein. (c) Boger, D. L.; Wolkenberg, S. E. J. Org. Chem. 2000, 65, 9120 and refs cited therein. (d) Pouysegu, L.; Avellan, A.-V.; Quideau, S. J. Org. Chem. 2002, 67, 3425 and refs cited therein.
47. For previous syntheses, see: (a) ref 21 and refs cited therein. (b) Miki, Y.; Shirokoshi, H.; Matsushita, K.-i. Tetrahedron Lett. 1999, 40, 4347 and refs cited therein. (c) Boger, D. L.; Wolkenberg, S. E. J. Org. Chem. 2000, 65, 9120 and refs cited therein. (d) Pouysegu, L.; Avellan, A.-V.; Quideau, S. J. Org. Chem. 2002, 67, 3425 and refs cited therein.
48. For previous syntheses, see: (a) ref 21 and refs cited therein. (b) Miki, Y.; Shirokoshi, H.; Matsushita, K.-i. Tetrahedron Lett. 1999, 40, 4347 and refs cited therein. (c) Boger, D. L.; Wolkenberg, S. E. J. Org. Chem. 2000, 65, 9120 and refs cited therein. (d) Pouysegu, L.; Avellan, A.-V.; Quideau, S. J. Org. Chem. 2002, 67, 3425 and refs cited therein.