Rapid synthesis of the ervitsine alkaloid skeleton by a sequential RCM-Heck cyclization approach

Synlett

Volumn , Issue 5, 2008, Pages 667-670

  Bennasar, M Lluïsa ^a   Zulaica, Ester ^a   Solé, Daniel ^a   Alonso, Sandra ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Alkaloids; Annulation; Heck reaction; Indoles; Metathesis

Indexed keywords

2 IODO 2 BUTENYLAMINE; ALKALOID; AMINE; IMINE; PALLADIUM; UNCLASSIFIED DRUG;

ALLYLATION; ANNULATION REACTION; ARTICLE; CATALYST; CYCLIZATION; METHYLATION; NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; SYNTHESIS;

EID: 41349086070     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1032102     Document Type: Article

References (38)

1. (a) Sundberg, R. J. Indoles; Academic Press: New York, 1996.
2. (b) Joule, J. A. Science of Synthesis (Houben-Weyl, Methods of Molecular Transformations), Vol. 10; Thieme: Stuttgart, 2000, 361.
3. (c) Somei, M.; Yamada, F. Nat. Prod. Rep. 2007, 24, 843; and previous reviews in this series.
4. For general reviews, see: (a) Handbook of Metathesis, Vol. 2; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003.
5. (b) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199.
6. For general reviews, see: (a) Bräse, S.; de Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A.; Diederich, F., Eds.; Wiley-WCH: New York, 2004, 217.
7. (b) Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644.
8. Joule, J. A. In Indoles, The Monoterpenoid Indole Alkaloids, Vol. 25; Saxton, J. E., Ed.; Wiley: New York, 1983, 232.
9. For previous synthetic work on ervitsine, see: (a) Bennasar, M.-L.; Vidal, B.; Bosch, J. J. Am. Chem. Soc. 1993, 115, 5340.
10. (b) Bennasar, M.-L.; Vidal, B.; Bosch, J. J. Org. Chem. 1997, 62, 3597.
11. (c) Bennasar, M.-L.; Zulaica, E.; Alonso, Y.; Bosch, J. Tetrahedron: Asymmetry 2003, 14, 469.
12. For previous work of the authors on RCM reactions of 2,3- dialkenylindoles, see: (a) Bennasar, M.-L.; Zulaica, E.; Tummers, S. Tetrahedron Lett. 2004, 45, 6283.
13. (b) Bennasar, M.-L.; Zulaica, E.; Alonso, S. Tetrahedron Lett. 2005, 46, 7881.
14. (c) Bennasar, M.-L.; Zulaica, E.; Solé, D.; Alonso, S. Tetrahedron 2007, 63, 861.
15. For the construction of benzo-fused bicyclic systems by sequential RCM and aryl halide Heck reactions, see: (a) Grigg, R.; Sridharan, V.; York, M. Tetrahedron Lett. 1998, 39, 4139.
16. (b) Grigg, R.; York, M. Tetrahedron Lett. 2000, 41, 7255.
17. (c) Lautens, M.; Zunic, V. Can J. Chem. 2004, 82, 399.
18. (d) Enders, D.; Lenzen, A.; Backes, M.; Janeck, C.; Catlin, K.; Lannou, M.-I.; Runsink, J.; Raabe, G. J. Org. Chem. 2005, 70, 10538.
19. For the construction of indolo-fused bicyclic system by sequential RCM and indolyl halide Heck cyclizations, see: (a) Sunderhaus, J. D.; Dockendorff, C.; Martin, S. F. Org. Lett. 2007, 9, 4223.
20. (b) Ribelin, T. P.; Judd, A. S.; Akritopoulou-Zanze, I.; Henry, R. F.; Cross, J. L.; Whittern, D. N.; Djuric, S. W. Org. Lett. 2007, 9, 5119.
21. (a) Rawal, V. H.; Michoud, C. Tetrahedron Lett. 1991, 32, 1695.
22. (b) Rawal, V. H.; Michoud, C.; Monestel, R. F. J. Am. Chem. Soc. 1993, 115, 3030.
23. (a) Rawal, V. H.; Iwasa, S. J. Org. Chem. 1994, 59, 2685.
24. (b) Solé, D.; Bonjoch, J.; García-Rubio, S.; Peidró, E.; Bosch, J. Chem. Eur. J. 2000, 6, 655.
25. (c) Eichberg, M. J.; Dorta, R. L.; Grotjahn, D. B.; Lamottke, K.; Schmidt, M.; Vollhardt, K. P. C. J. Am. Chem. Soc. 2001, 123, 9324.
26. Dounay, A. B.; Overman, L. E.; Wrobleski, A. D. J. Am. Chem. Soc. 2005, 127, 10186.
27. Birman, V. B.; Rawal, V. H. Tetrahedron Lett. 1998, 39, 7219.
28. Birman, V. B.; Rawal, V. H. J. Org. Chem. 1998, 63, 9146.
29. For instance, see: (a) Ban, Y.; Yoshida, K.; Goto, J.; Oishi, T.; Takeda, E. Tetrahedron 1983, 39, 3657.
30. (b) Gràcia, J.; Casamitjana, N.; Bonjoch, J.; Bosch, J. J. Org. Chem. 1994, 59, 3939.
31. (c) Saito, M.; Kawamura, M.; Hiroya, K.; Ogasawara, K. J. Chem. Commun. 1997, 765.
32. Prepared from (Z)-1,2-dibromo-2-butene or (Z)-1-bromo-2- iodo-2-butene.
33. Solé, D.; Urbaneja, X.; Cordero-Vargas, A.; Bonjoch, J. Tetrahedron 2007, 63, 10177.
34. (a) Jeffery, T. Tetrahedron Lett. 1985, 26, 2667.
35. (b) Jeffery, T. Tetrahedron 1996, 52, 10113.
36. Rutherford, J. L.; Rainka, M. P.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 15618.
37. See also: (a) Solé, D.; Urbaneja, X.; Bonjoch, J. Tetrahedron Lett. 2004, 45, 3131.
38. (b) Sole, D.; Urbaneja, X.; Bonjoch, J. Adv. Synth. Catal. 2004, 346, 1646.