From simple furans to complex nitrogen-bearing aromatic polycycles by means of a flexible and general reaction sequence initiated by singlet oxygen

Chemistry - A European Journal

Volumn 19, Issue 31, 2013, Pages 10119-10123

  Kalaitzakis, Dimitris ^a   Montagnon, Tamsyn ^a   Antonatou, Eirini ^a   Bardají, Nuria ^a   Vassilikogiannakis, Georgios ^a  

^a UNIVERSITY OF CRETE   (Greece)

Author keywords

erythrina alkaloids; N acyliminium; Pictet Spengler reaction; singlet oxygen; sustainable chemistry

Indexed keywords

N-ACYLIMINIUM; NATURAL PRODUCTS; ONE-POT REACTION; PICTET-SPENGLER REACTIONS; REACTION SEQUENCES; SINGLET OXYGEN; STRUCTURAL FEATURE; SUSTAINABLE CHEMISTRY;

ALKALOIDS; FUNCTIONAL GROUPS; METABOLITES; NITROGEN; NITROGEN COMPOUNDS; ORGANIC POLLUTANTS; OXYGEN;

AROMATIC COMPOUNDS;

EID: 84881388571     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201301571     Document Type: Article

References (65)

1. E. A. Anderson, Org. Biomol. Chem. 2011, 9, 3997-4006
2. K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292-7344
3. Angew. Chem. Int. Ed. 2006, 45, 7134-7186
4. L. F. Tietze, Chem. Rev. 1996, 96, 115-136.
5. "Synthesis Pathways to Erythrina Alkaloids and Erythrina Type Compounds":, E. Reimann, in Progress in the chemistry of Organic Natural Products, Vol. 88 (Eds.:, W. Herz, H. Falk, G. W. Kirby,), Springer, Wien, 2007, pp. 1-62.
6. W. N. Speckamp, H. Hiemstra, Tetrahedron 1985, 41, 4367-4416
7. B. E. Maryanoff, H.-C. Zhang, J. H. Cohen, I. J. Turchi, C. A. Maryanoff, Chem. Rev. 2004, 104, 1431-1628.
8. A. Pictet, T. Spengler, Ber. Dtsch. Chem. Ges. 1911, 44, 2030-2036
9. E. D. Cox, J. M. Cook, Chem. Rev. 1995, 95, 1797-1842.
10. S. M. Allin, J. M. R. Towler, M. R. J. Elsegood, B. Saha, P. C. B. Page, Synth. Commun. 2012, 42, 872-882
11. S. N. Gaskell, L. J. Duffy, S. M. Allin, Nat. Prod. Commun. 2008, 3, 1825-1838, and refs therein
12. S. M. Allin, S. L. James, W. P. Martin, T. A. D. Smith, Tetrahedron Lett. 2001, 42, 3943-3946.
13. I. T. Raheem, P. S. Thiara, E. N. Jacobsen, Org. Lett. 2008, 10, 1577-1580
14. I. T. Raheem, P. S. Thiara, E. A. Peterson, E. N. Jacobsen, J. Am. Chem. Soc. 2007, 129, 13404-13405.
15. E. García, S. Arrasate, E. Lete, N. Sotomayor, J. Org. Chem. 2005, 70, 10368-10374
16. A. Ardeo, E. García, S. Arrasate, E. Lete, N. Sotomayor, Tetrahedron Lett. 2003, 44, 8445-8448
17. E. García, S. Arrasate, A. Ardeo, E. Lete, N. Sotomayor, Tetrahedron Lett. 2001, 42, 1511-1513
18. M. I. Collado, I. Manteca, N. Sotomayor, M.-J. Villa, E. Lete, J. Org. Chem. 1997, 62, 2080-2092.
19. V. V. Komnatnyy, M. Givskov, T. E. Nielsen, Chem. Eur. J. 2012, 18, 16793-16800
20. E. Ascic, J. F. Jensen, T. E. Nielsen, Angew. Chem. 2011, 123, 5294-5297
21. Angew. Chem. Int. Ed. 2011, 50, 5188-5191.
22. A. Padwa, Q. Wang, J. Org. Chem. 2006, 71, 7391-7402
23. M. P. Cassidy, A. D. Özdemir, A. Padwa, Org. Lett. 2005, 7, 1339-1342
24. A. Padwa, A. G. Waterson, Tetrahedron 2000, 56, 10159-10173
25. A. Padwa, T. M. Heidelbaugh, J. T. Kuethe, M. S. McClure, Q. Wang, J. Org. Chem. 2002, 67, 5928-5937.
26. F. Zhang, N. S. Simpkins, A. J. Blake, Org. Biomol. Chem. 2009, 7, 1963-1979
27. F. Zhang, N. S. Simpkins, C. Wilson, Tetrahedron Lett. 2007, 48, 5942-5947
28. C. Gill, D. A. Greenhalgh, N. S. Simpkins, Tetrahedron Lett. 2003, 44, 7803-7807.
29. J. Liang, J. Chen, J. Liu, L. Li, H. Zhang, Chem. Commun. 2010, 46, 3666-3668.
30. M. D. Groaning, A. I. Meyers, Tetrahedron 2000, 56, 9843-9873
31. D. Romo, A. I. Meyers, Tetrahedron 1991, 47, 9503-9569.
32. C. A. Holloway, M. E. Muratore, R. I. Storer, D. J. Dixon, Org. Lett. 2010, 12, 4720-4723
33. M. E. Muratore, C. A. Holloway, A. W. Pilling, R. I. Storer, G. Trevitt, D. J. Dixon, J. Am. Chem. Soc. 2009, 131, 10796-10797.
34. M. M. Cid, D. Domínguez, L. Castedo, E. M. Vázquez- López, Tetrahedron 1999, 55, 5599-5610.
35. D. Fokas, Z. Wang, Synth. Commun. 2008, 38, 3816-3822.
36. M. Jida, O.-M. Soueidan, B. Deprez, G. Laconde, R. Deprez-Poulain, Green Chem. 2012, 14, 909-911.
37. M. D. Rose, M. P. Cassidy, P. Rashatasakhon, A. Padwa, J. Org. Chem. 2007, 72, 538-549
38. A. Padwa, H. I. Lee, P. Rashatasakhon, M. Rose, J. Org. Chem. 2004, 69, 8209-8218
39. A. Padwa, K. R. Crawford, P. Rashatasakhon, M. Rose, J. Org. Chem. 2003, 68, 2609-2617.
40. L. F. Tietze, N. Tölle, D. Kratzert, D. Stalke, Org. Lett. 2009, 11, 5230-5233
41. L. F. Tietze, N. Tölle, C. Noll, Synlett 2008, 525-528.
42. P. Gao, Y. Liu, L. Zhang, P.-F. Xu, S. Wang, Y. Lu, M. He, H. Zhai, J. Org. Chem. 2006, 71, 9495-9498.
43. H. H. Wasserman, R. M. Amici, J. Org. Chem. 1989, 54, 5843-5844.
44. E. Feng, Y. Zhou, F. Zhao, X. Chen, L. Zhang, H. Jiang, H. Liu, Green Chem. 2012, 14, 1888-1895.
45. E. Airiau, N. Girard, A. Mann, J. Salvadori, M. Taddei, Org. Lett. 2009, 11, 5314-5317.
46. W.-H. Chiou, G.-H. Lin, C.-C. Hsu, S. J. Chaterpaul, I. Ojima, Org. Lett. 2009, 11, 2659-2662.
47. Q. Q. He, C. M. Liu, K. Li, Chin. Chem. Lett. 2007, 18, 651-652
48. A. R. Katritzky, Y.-J. Xu, H.-Y. He, S. Mehta, J. Org. Chem. 2001, 66, 5590-5594
49. A. R. Katritzky, S. Mehta, H.-Y. He, J. Org. Chem. 2001, 66, 148-152
50. H. Fontaine, I. Baussanne, J. Royer, Synth. Commun. 1997, 27, 2817-2824
51. I. Baussanne, A. Chiaroni, H.-P. Husson, C. Riche, J. Royer, Tetrahedron Lett. 1994, 35, 3931-3934.
52. D. Noutsias, I. Alexopoulou, T. Montagnon, G. Vassilikogiannakis, Green Chem. 2012, 14, 601-604
53. T. Montagnon, D. Noutsias, I. Alexopoulou, M. Tofi, G. Vassilikogiannakis, Org. Biomol. Chem. 2011, 9, 2031-2039
54. T. Montagnon, M. Tofi, G. Vassilikogiannakis, Acc. Chem. Res. 2008, 41, 1001-1011.
55. We have recently been successful in accomplishing a similar cascade reaction sequence where trapping with an 1,2-aminoalcohol furnished Meyers' bicyclic lactam;, D. Kalaitzakis, T. Montagnon, I. Alexopoulou, G. Vassilikogiannakis, Angew. Chem. 2012, 124, 8998-9001
56. Angew. Chem. Int. Ed. 2012, 51, 8868-8871.
57. A. V. Stepakov, M. S. Ledovskaya, V. M. Boitsov, A. P. Molchanov, R. R. Kostikov, V. V. Gurzhiy, G. L. Starova, Tetrahedron Lett. 2012, 53, 5414-5417
58. I. Allous, S. Comesse, D. Berkeš, A. Alkyat, A. Daïch, Tetrahedron Lett. 2009, 50, 4411-4415
59. A. A. Bahajaj, J. M. Vernon, G. D. Wilson, J. Chem. Soc. Perkin Trans. 1 2001, 1446-1451
60. B. E. Maryanoff, D. F. McComsey, H. R. Almond, M. S. Mutter, G. W. Bemis, R. R. Whittle, R. A. Olofson, J. Org. Chem. 1986, 51, 1341-1346
61. B. E. Maryanoff, D. F. McComsey, B. A. Duhl-Emswiler, J. Org. Chem. 1983, 48, 5062-5074.
62. L. D. Miranda, S. Z. Zard, Org. Lett. 2002, 4, 1135-1138
63. S. Chikaoka, A. Toyao, M. Ogasawara, O. Tamura, H. Ishibashi, J. Org. Chem. 2003, 68, 312-318
64. A. Toyao, S. Chikaoka, Y. Takeda, O. Tamura, O. Muraoka, G. Tanabe, H. Ishibashi, Tetrahedron Lett. 2001, 42, 1729-1732
65. J. Cassayre, B. Quiclet-Sire, J.-B. Saunier, S. Z. Zard, Tetrahedron Lett. 1998, 39, 8995-8998.