Brønsted acid mediated cyclization of enaminones. Rapid and efficient access to the tetracyclic framework of the strychnos alkaloids

Journal of Natural Products

Volumn 75, Issue 2, 2012, Pages 181-188

  Edwankar, Rahul V ^a   Edwankar, Chitra R ^a   Namjoshi, Ojas A ^a   Deschamps, Jeffrey R ^b   Cook, James M ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

^b NAVAL RESEARCH LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AKUAMMILINE; ALKALOID; ASPIDOSPERMINE; BETA KETOESTER TETRAHYDRO BETA CARBOLINE; BRONSTED ACID; CARBOLINE DERIVATIVE; DIMETHYL 3 BENZYL 5 OXO 2,3,3A,4,5,6,6A,7 OCTAHYDRO 1H PYRROLO[2,3 D]CARBAZOLE 2,6 DICARBOXYLATE; METHYL 2 BENZYL 1 (4 METHOXY 2,4 DIOXOBUTYL) 2,3,4,9 TETRAHYDRO 1H PYRIDO[3,4 B]INDOLE 3 CARBOXYLATE; STRICTAMINE; UNCLASSIFIED DRUG;

ARTICLE; ASPIDOSPERMA; CHEMICAL BOND; CYCLIZATION; DRUG SYNTHESIS; NONHUMAN; STRYCHNOS;

ALKALOIDS; CYCLIZATION; INDOLE ALKALOIDS; MOLECULAR STRUCTURE; STEREOISOMERISM; STRYCHNOS;

ASPIDOSPERMA; STRYCHNOS;

EID: 84857525503     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np200759h     Document Type: Article

References (70)

1. For a review, see: Bosch, J.; Bonjoch, J.; Amat, M. The Strychnos Alkaloids. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1996; Vol. 48, pp 75-189.
2. Wiesner, K.; Rideout, W.; Manson, J. A. Experientia 1953, 9, 369
3. Rapoport, H.; Windgassen, R. J., Jr. ; Huges, N. A.; Onak, T. P. J. Am. Chem. Soc. 1960, 82, 4404-4414
4. Rapoport, H.; Onak, T. P.; Hughes, N. A.; Reinecke, M. G. J. Am. Chem. Soc. 1958, 80, 1601-1604
5. Janot, M.-M. Tetrahedron 1961, 14, 113-125
6. Rapoport, H.; Moore, R. E. J. Org. Chem. 1962, 27, 2981-2985
7. Mukherjee, R.; Da Silva, B. A.; Bagnolia, A.; Das, B. C.; Keifer, P. A.; Shoolery, J. N. Heterocycles 1991, 32, 985-990
8. Steele, J. C. P.; Veitch, N. C.; Kite, G. C.; Simmonds, M. S. J.; Warhurst, D. C. J. Nat. Prod. 2002, 65, 85-88
9. Dadson, B. A.; Harley-Mason, J. J. Chem. Soc. [Section D]., Chem. Commun. 1969, 665b
10. dos Santos, N. P.; Pinto, A. C.; de Alencastro, R. B. Quim. Nova 1998, 21, 666-670
11. Araújo, J. Q.; Lima, J. A.; Pinto, A. C.; de Alencastro, R. B.; Albuquerque, M. G. J. Mol. Model 2011, 17, 1401-1412
12. Lima, J. A.; Costa, R. S.; Epifânio, R. A.; Castro, N. G.; Rocha, M. S.; Pinto, A. C. Pharmacol. Biochem. Behav. 2009, 92, 508-513
13. Aurousseau, M. Ann. Pharm. Fr. 1961, 19, 175-189
14. Aurousseau, M. Ann. Pharm. Fr. 1961, 19, 104-116
15. Yu, S.; Berner, O. M.; Cook, J. M. J. Am. Chem. Soc. 2000, 122, 7827-7828
16. Wang, T.; Cook, J. M. Org. Lett. 2000, 2, 2057-2059
17. Edwankar, C. R.; Edwankar, R. V.; Rallapalli, S. K.; Cook, J. M. Nat. Prod. Commun. 2008, 3, 1839-1870
18. Edwankar, C. R.; Edwankar, R. V.; Namjoshi, O. A.; Rallapalli, S. K.; Yang, J.; Cook, J. M. Curr. Opin. Drug Discovery Dev. 2009, 12, 752-771
19. Cox, E.; Cook, J. M. Chem. Rev. 1995, 95, 1797-1842
20. Czerwinski, K. M.; Cook, J. M. Sterochemical Control of the Pictet-Spengler Reaction in the Synthesis of Natural Products. In Advances in Heterocyclic Natural Product Synthesis; Pearson, W., Ed.; Academic Press: San Diego, 1996; Vol. 3, pp 217-277.
21. Lorenz, M.; Van Linn, M. L.; Cook, J. M. Curr. Org. Synth. 2010, 7, 189-223
22. Lewis, S. E. Tetrahedron 2006, 62, 8655-8681
23. Jones, S. B.; Simmons, B.; Mastracchio, A.; MacMillan, D. W. C. Nature 2011, 475, 183-188
24. Delgado, R.; Blakey, S. B. Eur. J. Org. Chem. 2009, 1506-1510
25. Sirasani, G.; Andrade, R. B. Org. Lett. 2009, 11, 2085-2088
26. Martin, D. B. C.; Vanderwal, C. D. J. Am. Chem. Soc. 2009, 131, 3472-3473
27. Pereira, J.; Barlier, M.; Guillou, C. Org. Lett. 2007, 9, 3101-3103
28. Beniazza, R.; Dunet, J.; Robert, F.; Schenk, K.; Landais, Y. Org. Lett. 2007, 9, 3913-3916
29. Lynch, S. M.; Bur, S. K.; Padwa, A. Org. Lett. 2002, 4, 4643-4645
30. Hilton, S. T.; Jones, K.; Ho, T. C. T.; Pljevaljcic, G.; Schulte, M. Chem. Commun. 2001, 209-210
31. Mori, M.; Nakanishi, M.; Kajishima, D.; Sato, Y. Org. Lett. 2001, 3, 1913-1916
32. Doyle, M. P.; Mckervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides; Wiley-Interscience: New York, 1998.
33. Takano, S.; Shishido, K.; Sato, M.; Yuta, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1978, 943-944
34. Takano, S.; Shishido, K.; Sato, M.; Ogasawara, K. Heterocycles 1977, 6, 1699-1704
35. Takano, S.; Shishido, K.; Matsuzaka, J.; Sato, M.; Ogasawara, K. Heterocycles 1979, 13, 307-320
36. Harley-Mason, J.; Kaplan, M. Chem. Commun. 1967, 915-916
37. Yu, P.; Wang, T.; Li, J.; Cook, J. M. J. Org. Chem. 2000, 65, 3173-3191
38. Soerens, D.; Sandrin, J.; Ungemach, F.; Mokry, P.; Wu, G. S.; Yamanaka, E.; Hutchins, L.; DiPierro, M.; Cook, J. M. J. Org. Chem. 1979, 44, 535-545
39. Sandrin, J.; Soerens, D.; Hutchins, L.; Richfield, E.; Ungemach, F.; Cook, J. M. Heterocycles 1976, 4, 1101-1105
40. Valade, A.-G.; Dugat, D.; Jeminet, G.; Royer, J.; Husson, H.-P. Eur. J. Org. Chem. 2001, 2041-2053
41. Zaragoza, F.; Stephensen, H.; Peschke, B.; Rimvall, K. J. Med. Chem. 2005, 48, 306-311
42. Kumpaty, H. L.; Van Linn, M. L.; Kabir, M. S.; Försterling, F. H.; Deschamps, J. R.; Cook, J. M. J. Org. Chem. 2009, 74, 2771-2779
43. Sandrin, J.; Hollinshead, S. P.; Cook, J. M. J. Org. Chem. 1989, 54, 5636-5640
44. Brooks, D. W.; Lu, L. D.-L.; Masamune, S. Angew. Chem. Int. Ed. 1979, 18, 72-74
45. Poupardin, O.; Greck, C.; Genêt, J.-P. Synlett 1998, 1279-1281
46. Goundry, W. R. F. Synlett 2003, 1940-1941
47. Konkol, M.; Schmidt, H.; Steinborn, D. J. Mol. Catal. A: Chem. 2007, 269, 119-124
48. Singh, K.; Deb, P. K.; Venugopalan, P. Tetrahedron 2001, 57, 7939-7949
49. Elassar, A.-Z. A.; El-Khair, A. A. Tetrahedron 2003, 59, 8463-8480
50. Lu, P.; Greenhill, J. V. Enaminones in Heterocyclic Synthesis. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: San Diego, 1997; Vol. 67, pp 207-343. (Pubitemid 127820419)
51. Huizenga, R. H.; Pandit, U. K. Tetrahedron 1991, 47, 4155-4164
52. Büchi, G.; Matsumoto, K. E.; Nishimura, H. J. Am. Chem. Soc. 1971, 93, 3299-3301
53. Ando, M.; Büchi, G.; Ohnuma, T. J. Am. Chem. Soc. 1975, 97, 6880-6881
54. Hiemstra, H. C.; Bieräugel, H.; Pandit, U. K. Tetrahedron Lett. 1982, 23, 3301-3304
55. Akhrem, A. A.; Chernov, Y. G. Synthesis 1985, 411-412
56. Huizenga, R. H.; van Wiltenburg, J.; Bieräugel, H.; Pandit, U. K. Tetrahedron 1991, 47, 4165-4174
57. Huizenga, R. H.; Van Wiltenburg, J.; Pandit, U. K. Tetrahedron Lett. 1989, 30, 7105-7106
58. Pandit, U. K.; Bieräugel, H.; Stoit, A. R. Tetrahedron Lett. 1984, 25, 1513-1516
59. pKa Table.1. http://evans.harvard.edu/pdf/evans-pKa-table.pdf (accessed Dec 22, 2010).
60. Palmieri, G.; Cimarelli, C. Arkivoc 2006, 104-126
61. Greenhill, J. V. Chem. Soc. Rev. 1977, 6, 277-294
62. Ramírez, A.; García-Rubio, S. Curr. Med. Chem. 2003, 10, 1891-1915
63. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704-724
64. Wong, F. M.; Wang, J.; Hengge, A. C.; Wu, W. Org. Lett. 2007, 9, 1663-1665
65. Nakamura, E.; Yoshikai, N.; Yamanaka, M. J. Am. Chem. Soc. 2002, 124, 7181-7192
66. Sonawane, H. R.; Bellur, N. S.; Ahuja, J. R.; Kulkarni, D. G. J. Org. Chem. 1991, 56, 1434-1439
67. Hashimoto, S.; Watanabe, N.; Ikegami, S. Tetrahedron Lett. 1992, 33, 2709-2712
68. Cane, D. E.; Thomas, P. J. J. Am. Chem. Soc. 1984, 106, 5295-5303
69. Shen, L.; Zhang, M.; Wu, Y.; Qin, Y. Angew. Chem. Int. Ed. 2008, 47, 3618-3621
70. Danheiser, R. L.; Millar, R. F.; Brisbois, R. G.; Park, S. Z. J. Org. Chem. 1990, 55, 1959-1964