Stereocontrolled generation of benzo[a]- and indolo[2,3-a]quinolizidines from (S)-tryptophanol and (S)-(3,4-dimethoxyphenyl)alaninol-derived lactams

European Journal of Organic Chemistry

Volumn , Issue 20-21, 2011, Pages 3858-3863

  Pérez, Maria ^a   Arioli, Federica ^a   Rigacci, Gianna ^a   Santos, Maria M M ^b   Gõmez Esqué, Arantxa ^a   Escolano, Carmen ^a   Florindo, Pedro ^a   Ramos, Carlos ^a   Bosch, Joan ^a   Amat, Mercedes ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b RESEARCH INSTITUTE FOR MEDICINES IMED ULISBOA   (Portugal)

Author keywords

Alkaloids; Cyclization; Isomerization; Lactams; Nitrogen heterocycles

Indexed keywords

EID: 79960295012     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201100294     Document Type: Article

References (46)

1. J. Stöckigt, M. Ruppert, in: Comprehensive Natural Products (Eds.:, D. Barton, K. Nakanishi), Elsevier, New York, 1999, vol. 4, p. 109-138.
2. R. T. Brown, in: Indole and Biogenetically Related Alkaloids (Eds.:, J. D. Phillipson, M. H. Zenk), Academic Press, London, 1980, chapter 9.
3. N. Neuss, in: Indole and Biogenetically Related Alkaloids (Eds.:, J. D. Phillipson, M. H. Zenk), Academic Press, London, 1980, chapter 17.
4. R. T. Brown, in: Indoles-The Monoterpenoid Indole Alkaloids (Ed.:, J. E. Saxton), in: The Chemistry of Heterocyclic Compounds (Eds.:, A. Weissberger, E. C. Taylor), Wiley, New York, 1983, vol. 25, part 4, chapter 3.
5. R. T. Brown, in: The Chemistry and Biology of Isoquinoline Alkaloids (Eds.:, J. D. Phillipson, M. F. Roberts, M. H. Zenk), Springer-Verlag, Berlin, 1985, p. 204-212.
6. P. Dewick, in: Medicinal Natural Products-A Biosynthetic Approach, Wiley, Chichester, 2002.
7. M. Lounasmaa, A. Tolvanen, in: Monoterpenoid Indole Alkaloids (Ed.:, J. E. Saxton), in: The Chemistry of Heterocyclic Compounds (Ed.:, E. C. Taylor), Wiley, Chichester, 1994, vol. 25, part 4, chapter 3.
8. B. E. Maryanoff, H.-C. Zhang, J. H. Cohen, I. J. Turchi, C. A. Maryanoff, Chem. Rev. 2004, 104, 1431-1628.
9. J. Royer, M. Bonin, L. Micouin, Chem. Rev. 2004, 104, 2311-2352.
10. W. N. Speckamp, M. J. Moolenaar, Tetrahedron 2000, 56, 3817-3856.
11. M. Amat, M. M. M. Santos, O. Bassas, N. Llor, C. Escolano, A. Gõmez-Esqué, E. Molins, S. M. Allin, V. McKee, J. Bosch, J. Org. Chem. 2007, 72, 5193-5201.
12. For reviews about the use of chiral lactams as enantiomeric scaffolds, see D. Romo, A. I. Meyers, Tetrahedron 1991, 47, 9503-9569.
13. A. I. Meyers, G. P. Brengel, Chem. Commun. 1997, 1-8.
14. M. D. Groaning, A. I. Meyers, Tetrahedron 2000, 56, 9843-9873.
15. M. Amat, M. Pérez, J. Bosch, Synlett 2011, 143-160.
16. S. M. Allin, C. I. Thomas, K. Doyle, M. R. J. Elsegood, J. Org. Chem. 2005, 70, 357-359.
17. A. Gõmez-Esqué, Ph. D. Thesis, 2009, University of Barcelona.
18. S. M. Allin, D. G. Vaidya, S. L. James, J. E. Allard, T. A. D. Smith, V. McKee, W. P. Martin, Tetrahedron Lett. 2002, 43, 3661-3663.
19. B. E. Maryanoff, D. F. McComsey, B. A. Duhl-Emswiler, J. Org. Chem. 1983, 48, 5062-5074.
20. For the isomerization of amide derivatives of indolo[2,3-a]quinolizidines and related compounds, see G. Benz, H. Riesner, E. Winterfeldt, Chem. Ber. 1975, 108, 248-259.
21. S. Takano, S. Hatakeyama, K. Ogasawara, J. Am. Chem. Soc. 1979, 101, 6414-6420.
22. M. Node, H. Nagasawa, K. Fuji, J. Org. Chem. 1990, 55, 517-521.
23. M. Lounasmaa, M. Berner, M. Brunner, H. Suomalainen, A. Tolvanen, Tetrahedron 1998, 54, 10205-10216.
24. A. G. H. Wee, Q. Yu, J. Org. Chem. 2001, 66, 8935-5943.
25. A. Tosaka, S. Ito, N. Miyazawa, M. Shibuya, K. Ogasawara, Y. Iwabuchi, Heterocycles 2006, 70, 153-159.
26. J.-K. Chang, B.-R. Chang, Y.-H. Chuang, N.-C. Chang, Tetrahedron 2008, 64, 9685-9688.
27. W. Zhang, J. Franzén, Adv. Synth. Catal. 2010, 352, 499-518.
28. For the isomerization of amine derivatives of indolo[2,3-a] quinolizidines, see A. J. Gaskell, J. A. Joule, Tetrahedron 1967, 23, 4053-4063.
29. L.-H. Zhang, A. K. Gupta, J. M. Cook, J. Org. Chem. 1989, 54, 4708-4712.
30. M. Lounasmaa, L. Miikki, A. Tolvanen, Tetrahedron 1997, 53, 5349-5356.
31. M. Lounasmaa, M. Berner, A. Tolvanen, Heterocycles 1998, 48, 1275-1290.
32. C. Lohse, R. Detterbeck, P. Acklin, H.-J. Borschberg, Helv. Chim. Acta 2002, 85, 945-961.
33. For Pictet-Spengler cyclizations from (S)-tryptophan or (S)-tryptophanol derivatives, see H. Heaney, M. O. Taha, Tetrahedron Lett. 2000, 41, 1993-1996.
34. E. García, S. Arrasate, A. Ardeo, E. Lete, N. Sotomayor, Tetrahedron Lett. 2001, 42, 1511-1513.
35. S. M. Allin, S. L. James, W. P. Martin, T. A. D. Smith, M. R. J. Elsegood, J. Chem. Soc. Perkin Trans. 1 2001, 3029-3036.
36. A. Ardeo, E. García, S. Arrasate, E. Lete, N. Sotomayor, Tetrahedron Lett. 2003, 44, 8445-8448.
37. S. M. Allin, C. I. Thomas, J. E. Allard, M. Duncton, M. R. J. Elsegood, M. Edgar, Tetrahedron Lett. 2001, 42, 2335-2337.
38. M. M. Abelman, J. K. Curtis, D. R. James, Tetrahedron Lett. 2003, 44, 6527-6531.
39. A. S. Karpov, T. Oeser, T. J. J. Müller, Chem. Commun. 2004, 1502-1503.
40. E. García, S. Arrasate, E. Lete, N. Sotomayor, J. Org. Chem. 2005, 70, 10368-10374.
41. P. Deslongchamps, in: Stereoelectronic Effects in Organic Chemistry, Pergamon Press, Oxford, 1983, p. 221.
42. 2O, see S. M. Allin, S. N. Gaskell, M. R. J. Elsegood, W. P. Martin, J. Org. Chem. 2008, 73, 6448-6451. See also
43. M. D. Ennis, R. L. Hoffman, N. B. Ghazal, D. W. Old, P. A. Mooney, J. Org. Chem. 1996, 61, 5813-5817.
44. A. Castro, J. Ramírez, J. Juárez, J. L. Terán, L. Orea, A. Galindo, D. Gnecco, Heterocycles 2007, 71, 2699-2708.
45. D. Gnecco, A. M. Lumbreras, J. L. Terán, A. Galindo, J. R. Juárez, M. L. Orea, A. Castro, R. G. Enríquez, W. F. Reynolds, Heterocycles 2009, 78, 2589-2594.
46. L. F. Roa, D. Gnecco, A. Galindo, J. L. Terán, S. Bernès, Tetrahedron: Asymmetry 2004, 15, 847-850.