A synthetic entry to 2,3-fused ring indole derivatives by ring-closing metathesis reactions

Tetrahedron Letters

Volumn 45, Issue 33, 2004, Pages 6283-6285

  Bennasar, M Lluïsa ^a   Zulaica, Ester ^a   Tummers, Sven ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Indole alkaloids; Indoles; Ring closing metathesis

Indexed keywords

INDOLE ALKALOID;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PRECURSOR; RING CLOSING METATHESIS;

EID: 3242786301     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.06.097     Document Type: Article

References (38)

1. R.H. Grubbs Handbook of Metathesis Vol. 2 2003 Wileyâ€" VCH Weinheim
2. For selected reviews, see: R.H. Grubbs and S. Chang Tetrahedron 54 1998 4413 4450
3. A. FÃrstner Angew. Chem., Int. Ed. 39 2000 3012 3043
4. A.H. Hoveyda and R.R. Schrock Chem. Eur. J. 7 2001 945 950
5. For recent reviews on the application of RCM to the synthesis of heterocycles, see: M.A. Walters G.W. Gribble J.A. Joule Progress in Heterocyclic Chemistry Vol. 15 2003 Pergamon Amsterdam 1 36
6. A. Deiters and S.F. Martin Chem. Rev. 5 2004 2199 2238
7. C. Theeraladanon, M. Arisawa, A. Nishida and M. Nakagawa Tetrahedron 60 2004 3017 3035
8. M. Rosillo, G. DomÃnguez, L. Casarrubios, U. Amador and J. Pérez-Castells J. Org. Chem. 69 2004 2084 2093
9. For instance, see: S. Chang and R.H.J. Grubbs Org. Chem. 63 1998 864 866
10. W.A.L. van Otterlo, E.L. Ngidi, E.M. Coyanis and C.B. de Koning Tetrahedron Lett. 44 2003 311 313
11. C. Hardouin, L. Burgaud, A. Valleix and E. Doris Tetrahedron Lett. 44 2003 435 437
12. For instance, see: C. Lane and V. Snieckus Synlett 2000 1294 1296
13. W.A.L. van Otterlo, R. Pathak and C.B. de Koning Synlett 2003 1859 1861
14. S.J. Dolman, R.R. Schrock and A.H. Hoveyda Org. Lett. 5 2003 4899 4902
15. 1,2-Fused rings: V.B. Birman and V.H. Rawal J. Org. Chem. 63 1998 9146 9147
16. M.-P. Schramm, D.S. Reddy and S.A. Kozmin Angew. Chem., Int. Ed. 49 2001 4274 4277
17. P. González-Pérez, L. Pérez-Serrano, L. Casarrubios, G. DomÃ-nguez and J. Pérez-Castells Tetrahedron Lett. 43 2002 4765 4767
18. L. Chacun-LefÃvre, V. Bénéteau, B. Joseph and J.-Y. Mérour Tetrahedron 58 2002 10181 10188
19. 3,4-Fused carbocyclic rings: L. Pérez-Serrano, L. Casarrubios, G. DomÃ-nguez, G. Freire and J. Pérez-Castells Tetrahedron 58 2002 5407 5415
20. 3,4-Fused azacyclic systems: A. Kalinin, B.A. Chauder, S. Rahkit and V. Snieckus Org. Lett. 5 2003 3519 3521
21. R.J. Sundberg Indoles 1996 Academic New York
22. M.-L. Bennasar, T. Roca, R. Griera and J. Bosch Org. Lett. 3 2001 1697 1700
23. M.-L. Bennasar, T. Roca, R. Griera, M. Bassa and J. Bosch J. Org. Chem. 67 2002 6268 6271
24. M.-L. Bennasar, T. Roca and F. Ferrando Org. Lett. 6 2004 759 762
25. For a previous use of RCM for the construction of 2,3-fused ring indoles, see: N. Selvakumar, M.K. Khera, B.Y. Reddy, D. Srinivas, A.M. Azhagan and J. Iqbal Tetrahedron Lett. 44 2003 7071 7074
26. X. Yang, A. Althammer and P. Knochel Org. Lett. 6 2004 1665 1667 See also Ref. d
27. For synthesis of alkaloids of the ervitsine-ervatamine group, see: M.-L. Bennasar, B. Vidal and J. Bosch J. Org. Chem. 62 1997 3597 3609
28. M.-L. Bennasar, B. Vidal, R. Kumar, A. Lázaro and J. Bosch Eur. J. Org. Chem. 2000 3919 3925
29. M.-L. Bennasar, E. Zulaica, Y. Alonso and J. Bosch Tetrahedron: Asymmetry 14 2003 469 479
30. J.A. Joule J.E. Saxton Indoles, The Monoterpenoid Indole Alkaloids A. Weissberger E.C. Taylor The Chemistry of Heterocyclic Compounds Vol. 25 1983 Wiley New York Part 4, Chapter VI
31. M. Ishikura and M. Terashima J. Chem. Soc., Chem. Commun. 1989 727 728
32. Y. Kondo, N. Takazawa, A. Yoshida and T. Sakamoto J. Chem. Soc., Perkin Trans. 1 1995 1207 1208
33. It has been reported that alkene isomerizations sometimes interfere with the desired metathesis process. For discussions, see: B. Alcaide and P. Almendros Chem. Eur. J. 9 2003 1259 1262
34. B. Schmidt Angew. Chem., Int. Ed. 42 2003 4996 4999
35. Useful RCM-alkene isomerization sequences have been recently described, the latter process being promoted by in situ modified ruthenium catalysts: A.E. Sutton, B.A. Seigal, D.F. Finnegan and M.L. Snapper J. Am. Chem. Soc. 124 2002 13390 13391
36. B. Schmidt Eur. J. Org. Chem. 5 2003 816 819
37. B. Schmidt Chem. Commun. 2004 742 743
38. G.W. Gribble, J. Jiang and Y. Liu J. Org. Chem. 67 2002 1001 1003