Novel cyclo-dimerization of 1-tert-butoxycarbonyl-3-alkenylindole derivatives

Tetrahedron Letters

Volumn 46, Issue 7, 2005, Pages 1199-1203

  Kawasaki, Ikuo ^a   Terano, Masami ^a   Yada, Erika ^a   Kawai, Miwa ^a   Yamashita, Masayuki ^a   Ohta, Shunsaku ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; DICHLOROMETHANE; INDOLE DERIVATIVE; TRIFLUOROACETIC ACID;

ARTICLE; CRYSTAL STRUCTURE; DIMERIZATION; DRUG STRUCTURE; ROOM TEMPERATURE; STRUCTURE ANALYSIS;

EID: 12344311290     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.12.072     Document Type: Article

References (44)

1. For reviews see: S. Hibino, and T. Choshi Nat. Prod. Rep. 19 2002 148 180
2. D.J. Falkner Nat. Prod. Rep. 18 2001 1 49
3. M. Lounasmaa, and A. Nemes Tetrahedron 38 1982 223 243
4. Recent contributions: S. Zhao, X. Liao, T. Wang, J. Flippen-Anderson, and J.M. Cook J. Org. Chem. 68 2003 6279 6295
5. T. Kawasaki, T. Kouko, H. Totsuka, and K. Hiramatsu Tetrahedron Lett. 44 2003 8849 8852
6. F.Y. Miyake, K. Yakushijin, and D.A. Horn Org. Lett. 4 2002 941 943
7. B. Jiang, C.G. Yang, and J. Wang J. Org. Chem. 67 2002 1396 1398
8. C. Schneider Angew. Chem., Int. Ed. 41 2002 4217 4219
9. M.M. Faul, and K.A. Sullivan Tetrahedron Lett. 42 2001 3271 3273
10. T.S. Kam, T.M. Lim, and G.H. Tan J. Chem. Soc., Perkin Trans. 1 2001 1594 1604
11. M. Ishikura, K. Imaizumi, and N. Katagiri Heterocycles 53 2000 553 556
12. G. Lewin, C. Schaeffer, R. Hocquemiller, E. Jacoby, S. Léonce, A. Pierré, and G. Atassi Heterocycles 53 2000 2353 2356
13. S. Zhao, X. Liao, and J.M. Cook Org. Lett. 4 2002 687 690 and references cited therein
14. M. Bandini, M. Fagioli, A. Melloni, and A. Umani-Ronchi Synthesis 2003 397 402
15. J.Y. Su, Y. Zhu, L.M. Zeng, and X.H. Xu J. Nat. Prod. 60 1997 1043 1044
16. P.M. Fresneda, P. Molina, and M.A. Saez Synlett 1990 1651 1653
17. N. Wahlström, B. Stensland, and J. Bergman Tetrahedron 60 2004 2147 2153
18. I. Kawasaki, H. Katsuma, Y. Nakayama, M. Yamashita, and S. Ohta Heterocycles 48 1998 1887 1901
19. I. Kawasaki, M. Yamashita, and S. Ohta Chem. Pharm. Bull. 44 1996 1831 1839
20. I. Kawasaki, H. Katsuma, Y. Nakayama, M. Yamashita, and S. Ohta Heterocycl. Commun. 2 1996 189 191
21. I. Kawasaki, M. Yamashita, and S. Ohta Chem. Commun. 1994 2085 2086
22. T. Iwagawa, M. Miyazaki, H. Okamura, M. Nakatani, M. Doe, and K. Takemura Tetrahedron Lett. 44 2003 2533 2535
23. I. Mancini, G. Guella, H. Zibrowius, and F. Pietra Tetrahedron 59 2003 8757 8762
24. Y. Wolman Synthesis 1975 732
25. E. Akgün, and U.J. Pindur Heterocycl. Chem. 22 1985 585 591
26. A.-L. Johnson, J. Bergman, M. Sjögren, and L. Bohlin Tetrahedron 60 2004 961 965
27. L.N. Yudina, and J. Bergman Tetrahedron 59 2003 1265 1275
28. E.S. Tasber, and R.M. Garbaccio Tetrahedron Lett. 44 2003 9185 9188
29. M.L. Heredia, E. de la Cuesta, and C. Avendano Tetrahedron 58 2002 6163 6170
30. M.C. Bagley, S.L. Hind, and C.J. Moody Tetrahedron Lett. 41 2000 6897 6900
31. D.L. Boger, A. Santillan Jr., M. Searcey, S.R. Brunette, S.E. Wolkenberg, M.P. Hedrick, and Q. Jin J. Org. Chem. 65 2000 4101 4111
32. I. Hasan, E.R. Marinelli, L.-C.C. Lin, F.W. Fowler, and A.B. Levy J. Org. Chem. 46 1981 157 164
33. 3 (30 mL × 3). The organic layer was dried over anhydrous sodium sulfate and evaporated to give an oily residue, which was purified by silica gel column chromatography (n-hexane to AcOEt/n-hexane = 1/8) to give pure 4a (43 mg, 73%) as a pale yellow solid. Analytical sample was obtained by recrystallization from isopropyl ether (mp 239-240°C)
34. 2: C, 85.24; H, 7.66; N, 7.10. Found: C, 84.94; H, 7.88; N, 6.92
35. For review see: U. Pindur Heterocycles 27 1988 1253 1268
36. E.M. Beccalli, and A. Marchesini Tetrahedron 52 1996 3029 3036
37. X. Zhang, S.I. Khan, and C.S. Foote J. Org. Chem. 58 1993 7839 7847
38. U. Pindur, M.H. Kim, and M. Eitel Tetrahedron Lett. 31 1990 1551 1552
39. L. Pfeuffer, and U. Pindur Helv. Chim. Acta 71 1988 467 471
40. E. Wenkert, P.D.R. Moeller, S.R. Piettre, and A.T. McPhail J. Org. Chem. 53 1988 3170 3178
41. K.F. Cheng, Y.C. Kong, and T.Y. Chan Chem. Commun. 1985 48 49
42. J.R. Del Valle, and M. Goodman J. Org. Chem. 68 2003 3923 3931
43. H.H. Inhoffen, K.H. Nordsiek, and H. Schafer Liebigs Ann. Chem. 668 1963 104 121
44. 1/n. Crystallographic data (excluding structure factors) for the structure in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary number CCDC 257507. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk ]