Synthesis of polyalkylated indoles using a thallium(III)-mediated ring-contraction reaction

Synthesis

Volumn , Issue 24, 2007, Pages 3851-3857

  Silva Jr , Luiz F ^a   Craveiro, Marcus V ^a   Gambardella, Maria T P ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Cyclopenta g indoles; Ring contraction; Thallium trinitrate

Indexed keywords

ALKALOIDS; HERBINDOLS; RING CONTRACTION REACTIONS;

REACTION KINETICS; SYNTHESIS (CHEMICAL); THALLIUM COMPOUNDS;

NITROGEN COMPOUNDS;

1,6,7,8 TETRAHYDRO 6 DIMETHOXYMETHYL 1 TOSYLCYCLOPENTA[G]INDOLE; 8,9 DIHYDRO 1 TOSYL 1H BENZO[G]INDOLE; 8,9 DIHYDRO 1H BENZO[G]INDOLE; 8,9 DIHYDRO 3 TOSYL 1H BENZO[G]INDOLE; ALKALOID DERIVATIVE; INDOLE DERIVATIVE; TERT BUTYL 1H INDOLE 1 CARBOXYLATE; TERT BUTYL 2,3 DIMETHOXY 6 DIMETHOXYMETHYL 1,2,3,6,7,8 HEXAHYDROCYCLOPENTA[G]INDOLE 1(6H) CARBOXYLATE; TERT BUTYL 7,8 DIHYDRO 6 DIMETHOXYMETHYLCYCLOPENTA[G]INDOLE 1(6H) CARBOXYLATE; TERT BUTYL 8,9 DIHYDROBENZO[G]INDOLE 1 CARBOXYLATE; THALLIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; CRYSTAL STRUCTURE; DRUG OXIDATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

EID: 37549009080     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990907     Document Type: Article

References (55)

1. For some examples concerning the isolation of C2-C3 fused cycloalkylindoles, see: (a) Ondeyka, J. G.; Helms, G. L.; Hensens, O. D.; Goetz, M. A.; Zink, D. L.; Tsipouras, A.; Shoop, W. L.; Slayton, L.; Dombrowski, A. W.; Polishook, J. D.; Ostlind, D. A.; Tsou, N. N.; Ball, R. G.; Singh, S. B. J. Am. Chem. Soc. 1997, 119, 8809.
2. (b) Kato, L.; Braga, R. M.; Koch, I.; Kinoshita, L. S. Phytochemistry 2002, 60, 315.
3. (c) Singh, S. B.; Ondeyka, J. G.; Jayasuriya, H.; Zink, D. L.; Ha, S. N.; Dahl-Roshak, A.; Greene, J.; Kim, J. A.; Smith, M. M.; Shoop, W.; Tkacz, J. S. J. Nat. Prod. 2004, 67, 1496.
4. (d) Carrol, A. R.; Hyde, E.; Smith, J.; Quinn, R. J.; Guymer, G.; Forster, P. I. J. Org. Chem. 2005, 70, 1096.
5. For some examples concerning the synthesis of C2-C3 fused cycloalkylindoles, see: (a) Giannini, G.; Marzi, M.; Moretti, G. P.; Penco, S.; Tinti, M. O.; Pesci, S.; Lazzaro, F.; De Angelis, F. Eur. J. Org. Chem. 2004, 2411.
6. (b) Maertens, F.; Van den Bogaert, A.; Compernolle, F.; Hoornaert, G. J. Eur. J. Org. Chem. 2004, 4648.
7. (c) Smith, A. B. III.; Kurti, L.; Davulcu, A. H. Org. Lett. 2006, 8, 2167.
8. (d) Sturino, C. F.; Lachance, N.; Boyd, M.; Berthelette, C.; Labelle, M.; Li, L.; Roy, B.; Scheigetz, J.; Tsou, N.; Brideau, C.; Cauchon, E.; Carriere, M.-C.; Denis, D.; Greig, G.; Kargman, S.; Lamontagne, S.; Mathieu, M.-C.; Sawyer, N.; Slipetz, D.; O'Neill, G.; Wang, Z.; Zamboni, R.; Metters, K. M.; Young, R. N. Bioorg. Med. Chem. Lett. 2006, 16, 3043.
9. (a) Capon, R. J.; MacLeod, J. K.; Scammels, P. J. Tetrahedron 1986, 42, 6545.
10. (b) Herb, R.; Carrol, A. R.; Yoshida, W. Y.; Scheuer, P. J.; Paul, V. J. Tetrahedron 1990, 46, 3089.
11. Sawyer, J. S.; Beight, D. W.; Smith, E. C. R.; Snyder, D. W.; Chastain, M. K.; Tielkin, R. L.; Hartley, L. W.; Carlson, D. G. J. Med. Chem. 2005, 48, 893.
12. (a) MacLeod, J. K.; Monahan, L. C. Tetrahedron Lett. 1988, 29, 391.
13. (b) Muratake, H.; Natsume, M. Tetrahedron Lett. 1989, 30, 5771.
14. (c) Muratake, H.; Watanabe, M.; Goto, K.; Natsume, M. Tetrahedron 1990, 46, 4179.
15. (d) MacLeod, J. K.; Monahan, L. C. Aust. J. Chem. 1990, 43, 329.
16. (e) Boger, D. L.; Zhang, M. J. Am. Chem. Soc. 1991, 113, 4230.
17. (f) Muratake, H.; Mikawa, A.; Natsume, M. Tetrahedron Lett. 1992, 33, 4595.
18. (g) Muratake, H.; Seino, T.; Natsume, M. Tetrahedron Lett. 1993, 34, 4815.
19. (h) Wiedenau, P.; Monse, B.; Blechert, S. Tetrahedron 1995, 51, 1167.
20. (i) MacLeod, J. K.; Ward, A.; Willis, A. C. Aust. J. Chem. 1998, 51, 177.
21. (j) Jackson, S. K.; Banfield, S. C.; Kerr, M. A. Org. Lett. 2005, 7, 1215.
22. (k) Huntley, R. J.; Funk, R. L. Org. Lett. 2006, 8, 3403.
23. (l) Jackson, S. K.; Kerr, M. A. J. Org. Chem. 2007, 72, 1405.
24. For some reviews concerning thallium(III) in organic synthesis, see: (a) McKillop, A.; Taylor, E. C. In Comprehensive Organometallic Chemistry, Vol. 7; Wilkinson, G., Ed.; Pergamon Press: New York, 1982, 465.
25. (b) Ferraz, H. M. C.; Silva, L. F. Jr.; Vieira, T. O. Synthesis 1999, 2001.
26. (c) Uemura, S. In Synthetic Reagents, Vol. 5; Pizey, J. S., Ed.; Ellis Horwood: Chichester, 1983, 164.
27. For some examples of rearrangement of olefins with TTN, see: (a) McKillop, A.; Hunt, J. D.; Taylor, E. C.; Kienzle, F. Tetrahedron Lett. 1970, 11, 5275.
28. (b) McKillop, A.; Hunt, J. D.; Kienzle, F.; Bigham, E.; Taylor, E. C. J. Am. Chem. Soc. 1973, 95, 3635.
29. (c) Taylor, E. C.; Chiang, C.-S.; McKillop, A.; White, J. F. J. Am. Chem. Soc. 1976, 98, 6750.
30. (d) Rigby, J. H.; Pigge, F. C. J. Org. Chem. 1995, 60, 7392.
31. (e) Rigby, J. H.; Pigge, F. C. Synlett 1996, 631.
32. (f) Butkus, E.; Zilinskas, A.; Stoncius, S.; Rozembergas, R.; Urbanová, M.; Setnicka, V.; Boui, P.; Volka, K. Tetrahedron: Asymmetry 2002, 13, 633.
33. (g) Singh, O. V.; Muthukrishnan, M.; Sundaravedivelu, M. Synth. Commun. 2006, 36, 946.
34. (a) Ferraz, H. M. C.; Silva, L. F. Jr.; Vieira, T. O. Tetrahedron 2001, 57, 1709.
35. (b) Ferraz, H. M. C.; Aguilar, A. M.; Silva, L. F. Jr. Tetrahedron 2003, 59, 5817.
36. (c) Silva, L. F. Jr.; Sousa, R. M. F.; Ferraz, H. M. C.; Aguilar, A. M. J. Braz. Chem. Soc. 2005, 16, 1160.
37. (d) Silva, L. F. Jr.; Quintiliano, S. A. P.; Craveiro, M. V.; Vieira, F. Y. M.; Ferraz, H. M. C. Synthesis 2007, 355.
38. (e) For a related reaction using iodine(III), see: Silva, L. F. Jr.; Siqueira, F. A.; Pedrozo, E. C.; Vieira, F. Y. M.; Doriguetto, A. C. Org. Lett. 2007, 9, 1433.
39. (a) Somei, M.; Hasegawa, T.; Kaneko, C. Heterocycles 1983, 20, 1983.
40. (b) Somei, M.; Saida, Y.; Funamoto, T.; Ohta, T. Chem. Pharm. Bull. 1987, 35, 3146.
41. (c) Banerji, A.; Nandi, G. Heterocycles 1987, 26, 1221.
42. (d) Tholander, J.; Bergman, J. Tetrahedron 1999, 55, 12595.
43. Desarbre, E.; Savelon, L.; Cornec, O.; Mérour, J. Y. Tetrahedron 1996, 52, 2983.
44. The X-ray crystal structure data have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 656449. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: + 44 1223 336 033; e-mail: deposit@ccdc.cam.ac.uk).
45. (a) Anderson, C. B.; Winstein, S. J. Org. Chem. 1963, 28, 605.
46. (b) Abley, P.; Byrd, J. E.; Halpern, J. J. Am. Chem. Soc. 1973, 95, 2591.
47. Zhang, M.; Schuster, G. B. J. Am. Chem. Soc. 1994, 116, 4852.
48. Bartoli, G.; Palmieri, G.; Bosco, M.; Dalpozzo, R. Tetrahedron Lett. 1989, 30, 2129.
49. Michael, J. P.; Nkwelo, M. M. Tetrahedron 1990, 46, 2549.
50. A complex mixture was obtained when 9 was treated with 1.1 equiv of TTN in MeOH at 0°C.
51. Ghren, L.; Ragnarsson, U. Angew. Chem. Int. Ed. 1984, 23, 296.
52. Ottoni, O.; Cruz, R.; Alves, R. Tetrahedron 1998, 54, 13915.
53. (a) Lee, J. B.; Price, M. J. Tetrahedron 1964, 20, 1017.
54. (b) Sekizaki, H.; Ito, M.; Inoue, S. Bull. Chem. Soc. Jpn. 1978, 51, 2439.
55. Seyferth, D. Org. Synth. Coll. Vol. 4; Wiley: New York, 1963, 258.