Efficient synthetic approaches to the common scaffold of indole alkaloids

Organic Letters

Volumn 9, Issue 20, 2007, Pages 3913-3916

  Beniazza, Redouane ^a   Dunet, Julie ^a   Robert, Frédéric ^a   Schenk, Kurt ^b   Landais, Yannick ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

^b UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 35048865728     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701493k     Document Type: Article

References (45)

1. Saxton, J. E. In The Alkaloids, Alkaloids of the Aspidospermine Group; Cordell, G. A., Ed.; Academic Press: New York, 1998; Vol. 51, p 1.
2. (a) Saxton, J. E. Nat. Prod. Rep. 1995, 385.
3. (b) Kuehne, M. E.; Podhorez, D. E.; Mulamba, T.; Bornmann, W. G. J. Org. Chem. 1987, 52, 347.
4. (c) Mangeney, P.; Andriamialisoa, R. Z.; Langlois, N.; Langlois, Y.; Potier, P. J. Am. Chem. Soc. 1979, 101, 2243.
5. (a) Scott, A. I. Acc. Chem. Res. 1970, 3, 151.
6. (b) Wenkert, E. J. Am. Chem. Soc. 1962, 84, 98.
7. (a) Saxton, J. E. In The Alkaloids, Synthesis of Aspidosperma Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1998; Vol. 50, p 343 and refs cited.
8. (b) Kuehne, M. E.; Kirkemo, C. L.; Matsko, T. H.; Bohnert, J. C. J. Org. Chem. 1980, 45, 3259.
9. (a) Ando, M.; Büchi, G.; Ohnuma, T. J. Am. Chem. Soc. 1975, 97, 6880.
10. (b) Heureux, N.; Wouters, J.; Marko, I. E. Org. Lett. 2005, 7, 5245.
11. (a) Tietze, L. F. Chem. Rev. 1996, 96, 115.
12. (b) Poli, G.; Giambastani, G.; Heumann, A. Tetrahedron 2000, 56, 5959.
13. (a) Abd Rahman, N.; Landais, Y. Curr. Org. Chem. 2002, 6, 1369.
14. (b) Studer, A.; Schleth, F. Synlett 2005, 3033.
15. (c) Lebeuf, R.; Robert, F.; Landais, Y. Org. Lett. 2006, 8, 4755.
16. Lebeuf, R.; Robert, F.; Landais, Y. Org. Lett. 2005, 7, 4557.
17. (a) Rogers, M. M.; Wendlandt, J. E.; Guzei, I. A.; Stahl, S. S. Org. Lett. 2006, 8, 2257.
18. (b) Fix, S. R.; Brice, J. L.; Stahl, S. S. Angew. Chem., Int. Ed. 2002, 41, 164.
19. (c) Bäckvall, J.-E.; Andersson, P. G. J. Am. Chem. Soc. 1990, 112, 3683.
20. (d) Verboom, R. C.; Persson, B. A.; Bäckvall, J.-E. J. Org. Chem. 2004, 69, 3102.
21. (e) Hosokawa, T.; Miyagi, S.; Murahashi, S.-I.; Sonoda, A. J. Org. Chem. 1978, 43, 2752.
22. (f) Hegedus, L. S.; McKearin, J. M. J. Am. Chem. Soc. 1982, 104, 2444.
23. (a) van Benthem, R. A. T. M.; Hiemstra, H.; Longarela, G. R.; Speckamp, W. N. Tetrahedron Lett. 1994, 35, 9281.
24. (b) Rönn, M.; Bäckvall, J.-E.; Andersson, P. G. Tetrahedron Lett. 1995, 36, 7749.
25. (c) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584.
26. (a) Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400.
27. (b) Gligorich, K. M.; Sigman, M. S. Angew. Chem., Int. Ed. 2006, 45, 6612.
28. Deposition of black Pd metal was effectively observed in some cases.
29. (a) Mahaim, C.; Carrupt, P.-A.; Hagenbuch, J-P.; Florey, A.; Vogel, P. Helv. Chim. Acta 1980, 63, 1149.
30. (b) Steunenberg, P.; Jeanneret, V.; Zhu, Y.-H.; Vogel, P. Tetrahedron: Asymmetry 2005, 16, 337.
31. We noticed that quenching the reaction between 8a,b and Pd(OAc)2 before complete consumption of the starting material led to the formation in a small amount of a monocyclized product analogous to 7.
32. Wim 1,4-dienes, allylic C - H activation followed by amination of the resulting π-allyl-Pd(II) intermediate might also be considered. For recent studies, see: Fraunhoffer, K. J.; White, M. C. J. Am. Chem. Soc. 2007, 129, 7274.
33. 10
34. Trapping of π-allyl-Pd(II) intermediates such as V with various nucleophiles in an intramolecular fashion has led so far to low yield of the desired pentacyclic systems. Investigations on this approach are still in progress.
35. This feature is important in the context of the functionalization of this ring for the synthesis of Aspidosperma and Iboga alkaloids.
36. (a) Martin, S. F.; Campbell, C. L. J. Org. Chem. 1988, 53, 3184.
37. (b) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1995, 117, 11106.
38. (c) Bland, D.; Chambournier, G.; Dragan, V.; Hart, D. J. Tetrahedron 1999, 55, 8953.
39. (d) Bru, C.; Guillou, C. Tetrahedron 2006, 62, 9043.
40. (a) Page, P. C. B.; McCarthy, T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon: Oxford, 1991; Vol. 7, p 83.
41. (b) Müller, P. M.; Pfister, R. Helv. Chim. Acta 1983, 66, 111.
42. (c) Shing, T. K. M.; Yeung, Y.-Y.; Su, P. L. Org. Lett. 2006, 8, 3149.
43. (a) Yu, J.-Q.; Corey, E. J. Org. Lett. 2002, 4, 2727.
44. 2-t-BuOOH led to a similar result.
45. 2NEt).