Concise catalytic asymmetric total synthesis of biologically active tropane alkaloids

Advanced Synthesis and Catalysis

Volumn 354, Issue 7, 2012, Pages 1363-1372

  Cõrdova, Armando ^a,b   Lin, Shuangzheng ^a   Tseggai, Abrehet ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b MID SWEDEN UNIVERSITY   (Sweden)

Author keywords

asymmetric catalysis; cocaine; cycloadditions; ferruginine; multi component reactions; stereoselectivity; tandem reactions

Indexed keywords

EID: 84860777813     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100917     Document Type: Article

References (69)

1. P. P. Gian, B. Simonetta, D. Carmela, Z. Vinicio, Chem. Rev. 2006, 106, 243.
2. D. O'Hagan, Nat. Prod. Rep. 2000, 17, 435
3. D. O'Hagan, Nat. Prod. Rep. 1997, 14, 637
4. G. Fodor, R. Dharanipragada, Nat. Prod. Rep. 1994, 11, 443
5. M. Lounasmaa, T. Tamminen, in: The Tropane Alkaloids in Alkaloids, Academic Press, New York, 1993, p 1
6. A. J. Humphrey, D. O'Hagan, Nat. Prod. Rep. 2001, 18, 494.
7. F. I. Carroll, A. H. Lewin, J. W. Boja, M. J. Kuhar, J. Med. Chem. 1992, 35, 969
8. G. F. Koob, F. E. Bloom, Science 1988, 242, 715.
9. K. L. Swanson, E. X. Albuquerque, in: Handbook of Experimental Pharmacology, Vol. 102, Selective Neurotoxicity, (Eds.:, H. Herken, F. Hucho,), Springer, Berlin, 1992, p 620.
10. D. Gündisch, T. Kämpchen, S. Schewarz, G. Seitz, J. Siegl, T. Wegge, Bioorg. Med. Chem. 2002, 10, 1
11. D. Gündisch, K. Harms, S. Schewarz, G. Seitz, M. T. Stubbs, T. Wegge, Bioorg. Med. Chem. 2001, 9, 2683.
12. For example, (R)-(-)-cocaine 1 is 155 times more potent than its mirror image (S)-(+)-cocaine ent- 1, which is rapidly metabolized., S. J. Gatley, R. R. MacGregor, J. S. Fowler, A. P. Wolf, S. L. Dewey, D. J. Schlyer, J. Neurochem. 1990, 54, 720.
13. S. C. Laizure, T. Mandrell, N. M. Gades, R. B. Parker, Drug Metab. Dispos. 2003, 31, 16, and references cited therein.
14. F. I. Carroll, B. E. Blough, S. W. Mascarella, H. A. Navarro, J. B. Eaton, R. J. Lukas, M. I. Damaj, J. Med. Chem. 2010, 53, 8345-8353
15. P. J. Riss, R. Hummerich, P. Schloss, Org. Biomol. Chem. 2009, 7, 2688-2698
16. F. I. Carroll, S. Tyagi, B. E. Blough, M. J. Kuhar, H. A. Navarro, J. Med. Chem. 2005, 48, 3852-3857
17. L. Xu, S. S. Kulkarni, S. Izenwasser, J. L. Katz, T. Kopajtic, S. A. Lomenzo, A. H. Newman, M. L. Trudell, J. Med. Chem. 2004, 47, 1676-1682
18. R. H. Kline Jr, J. Wright, K. M. Fox, M. E. Eldefrawi, J. Med. Chem. 1990, 33, 2024-2027
19. R. L. Clarke, S. J. Daum, A. J. Gambino, M. D. Aceto, J. Pearl, M. Levitt, W. R. Cumiskey, E. F. Bogado, J. Med. Chem. 1973, 16, 1260.
20. R. Willstätter, W. Müller, Ber. Dtsch. Chem. Ges. 1898, 31, 2655
21. R. Willstätter, D. Wolfes, H. Mäder, Ann. Chem. Zeitschrift wurde erst 1959 geründet! 1923, 434, 11.
22. R. Robinson, J. Chem. Soc. 1917, 111, 762.
23. G. P. Pollini, S. Benetti, C. De Risi, V. Zanirato, Chem. Rev. 2006, 106, 2434
24. G. Fodor, Tetrahedron 1957, 13, 86
25. S. Sing, Chem. Rev. 2011, 100, 925
26. A. H. Lewin, T. Naseree, F. I. Carroll, J. Heterocycl. Chem. 1987, 24, 19
27. J. Cruses, R. Jaouhari, J. O'Callaghan, J. Tojo, PharmaChem. 2002, March, 9.
28. G. Cheng, X. Wang, R. Zhu, C. Shao, J. Xu, Y. Hu, J. Org. Chem. 2011, 76, 2694
29. T. K. M. Shing, K. H. So, Org. Lett. 2011, 13, 2916
30. F. A. Davis, N. Theddu, R. Edupuganti, Org. Lett. 2010, 12, 4118
31. D. M. Mans, W. H. Pearson, Org. Lett. 2004, 6, 3305
32. J. C. Lee, K. Lee, J. K. Cha, J. Org. Chem. 2000, 65, 4773
33. R. Lin, J. Castells, H. Rapport, J. Org. Chem. 1998, 63, 4069.
34. V. K. Aggarwal, C. J. Astle, M. Rogers-Evans, Org. Lett. 2004, 6, 1469
35. T. Katoh, K. Kakiya, T. Nakai, S. Nakamura, K. Nishide, M. Node, Tetrahedron: Asymmetry 2002, 13, 2351
36. S. Y. Jonsson, C. M. G. Löfström, J.-E. Bäckvall, J. Org. Chem. 2000, 65, 8454
37. A. S. Hernández, A. Thaler, J. Castells, H. Rapoport, J. Org. Chem. 1996, 61, 314
38. J. H. Rigby, F. C. Pigge, J. Org. Chem. 1995, 60, 7392. For the synthesis of (-)-ferrunginine also see
39. H. M. L. Davies, J. J. Matasi, L. M. Hodges, N. J. S. Huby, C. Thornley, N. Kong, J. H. Houser, J. Org. Chem. 1997, 62, 1095.
40. G. L. Zhao, S. Lin, A. Korotvicka, L. Deiana, M. Kullberg, A. Cõrdova, Adv. Synth. Catal. 2010, 352, 2291
41. J. Casas, M. Engqvist, I. Ibrahem, B. Kaynak, A. Cõrdova, Angew. Chem. 2005, 117, 1367
42. Angew. Chem. Int. Ed. 2005, 44, 1343
43. I. Ibrahem, W. Zou, J. Casas, H. Sundén, A. Cõrdova, Tetrahedron 2006, 62, 357
44. S. Lin, L. Deiana, A. Tseggai, A. Cõrdova, Eur. J. Org. Chem. 2012, 398
45. W.-W. Liao, I. Ibrahem, A. Cõrdova, Chem. Commun. 2006, 674.
46. P. Anastas, J. Warner, Green Chemistry: Theory and Practice, Oxford University Press, New York, 1998.
47. D. J. Ramon, M. Yus, Angew. Chem. 2005, 117, 1628
48. Angew. Chem. Int. Ed. 2005, 44, 1602
49. L. F. Tietze, A. Dürfert, Catalytic Asymmetric Conjugate Reactions, (Ed.:, A. Cõrdova,), Wiley-VCH, Weinheim, 2010, p 321
50. L. F. Tietze, Chem. Rev. 1996, 96, 115
51. K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292
52. Angew. Chem. Int. Ed. 2006, 45, 7134
53. H. Guo, J. Ma, Angew. Chem. 2006, 118, 362
54. Angew. Chem. Int. Ed. 2006, 45, 354
55. H. Pellieser, Tetrahedron 2006, 62, 2143
56. J. Zhu, H. Bienayme, Multicomponent Reactions, Wiley-VCH, Weinheim, 2005.
57. For a paper on collected synthesis of natural products in combination with organocascade catalysis, see:, S. B. Jones, B. Simmons, A. Mastracchio, D. W. C. MacMillan, Nature 2011, 183.
58. K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292
59. Angew. Chem. Int. Ed. 2006, 45, 7134
60. P. J. Parsons, C. S. Penkett, A. J. Shell, Chem. Rev. 1996, 96, 195.
61. J. Vesely, I. Ibrahem, R. Rios, G.-L. Zhao, Y. Xu, A. Cõrdova, Tetrahedron Lett. 2007, 48, 2193.
62. Y. K. Chen, M. Yoshida, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 9328.
63. J. J. Tufariello, G. B. Mullen, J Am. Chem. Soc. 1978, 100, 3638.
64. W.-M. Chen, H. N. C. Wong, D. T. W. Chu, X. Lin, Tetrahedron 2003, 59, 7033
65. M. Sakaitani, Y. Ohfune, J. Org. Chem. 1990, 55, 870.
66. M.-F. Zou, T. Kopajtic, J. L. Katz, S. Wirtz, J. B. Justice Jr, A. H. Newman, J. Med. Chem. 2001, 44, 4453.
67. M. R. A Carrera, J. A. Ashley, B. Zhou, P. Wirsching, G. F. Koob, K. D. Janda, Nature 1995, 378, 727
68. M. M. Meijler, M. Matsushita, P. Wirsching, K. D. Janda, Curr. Drug Discovery Technol. 2004, 1, 77
69. D. W. Landry, K. Zhao, G. X. P. Yang, M. Glickman, T. M. Georgiadis, Science 1993, 259, 1899.