Expedious and practical synthesis of the bioactive alkaloids rutaecarpine, euxylophoricine A, deoxyvasicinone and their heterocyclic homologues

Tetrahedron Letters

Volumn 47, Issue 11, 2006, Pages 1777-1781

  Hamid, Abdulkareem ^a   Elomri, Abdelhakim ^b   Daïch, Adam ^a  

^a UNIVERSITÉ DU HAVRE   (France)

^b Laboratoire Quant If   (France)

Author keywords

Alkaloid; Bioactive product; Heterocycle; Imino thioether; Lawesson's; One pot procedure; Peptedic coupling; Thioether; Thionation

Indexed keywords

ALKALOID DERIVATIVE; AROMATIC AMINO ACID; CARBOLINE DERIVATIVE; DEOXYVASICINONE; ESTER DERIVATIVE; ETHER DERIVATIVE; EUXYLOPHORICINE A; HETEROCYCLIC COMPOUND; PYRIMIDO BETA CARBOLINE DERIVATIVE; RUTAECARPINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; CYCLODEHYDRATION; DRUG ACTIVITY; DRUG SYNTHESIS; METHODOLOGY;

EID: 32244446311     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.01.031     Document Type: Article

References (67)

1. For reviews, see: S. Johne, and D. Groger Pharmazie 25 1970 22 44
2. G.M. Coppola Synthesis 1980 505 536
3. S. Johne Prog. Drug Res. 26 1982 259 341
4. S. Johne Prog. Chem. Org. Nat. Prod. 46 1984 159 229
5. J.P. Michael Nat. Prod. Rep. 17 2000 603 620
6. A. Witt, and J. Bergman Curr. Org. Chem. 7 2003 659 677
7. J.H. Chu Sci. Rec. (China) 4 1951 279 284
8. Chem. Abstr. 46 1952 11589b
9. For isolation of rutaecarpine (1a ), see: Y. Asahina, and K. Kashiwaki Yakugaku Zasshi 405 1915 1273 1293
10. Y. Asahina Acta Phytochim. 1 1922 67 70
11. For the first report of rutaecarpine (1a ), see: Y. Asahina, R.H.F. Manske, and R. Robinson J. Chem. Soc. 1927 708 1710
12. See, for example, A.L. Chen, and K.K. Chen J. Am. Pharm. Assoc. 22 1933 716 719
13. T.-S. Wu, J.-H. Yeh, P.-L. Wu, K.-T. Chen, L.-C. Lin, and C.-F. Chen Heterocycles 41 1995 1071 1076
14. A. Ikuta, H. Urabe, and T. Nakamura J. Nat. Prod. 61 1998 1012 1014
15. X.-C. Lia, D.C. Dunbar, H.N. El-Sohlya, L.A. Walker, and A.M. Clark Phytochemistry 58 2001 627 629
16. E. Christopher, E. Bedir, C. Dunbar, I.A. Khan, C.O. Okunji, B.M. Schuster, and M.M. Iwu Helv. Chem. Acta 86 2003 2914 2918
17. C. Wattanapiromsakul, P.I. Forster, and P.G. Waterman Phytochemistry 64 2003 609 615
18. H. Matsuda, M. Yoshikawa, S. Ko, M. Iinuma, and M. Kubo Nat. Med. 52 1998 203 206
19. T.C. Moon, M. Murakami, I. Kudo, K.H. Son, H.P. Kim, S.S. Kang, and H.W. Chang Inflamm. Res. 4 1999 621 625
20. H.G. Woo, C.H. Lee, M.-S. Noh, J.J. Lee, Y.-S. Jung, E.J. Baik, C.-H. Moon, and S.H. Lee Planta Med. 67 2001 505 509
21. Y.C. Kong, H.A. Hu, K.F. Lu, C.T. Che, H.W. Yeng, S. Cheng, and C.C. Hwang Am. J. Chin. Med. 4 1976 105 128
22. W. Tang, and G.E. Eisenbrand Chinese drugs of plant origin. 1992 Springer Berlin p 508
23. S. Hibino, and T. Choshi Nat. Prod. Rep. 18 2001 66 87
24. J. Bergman A.R. Brossi The Alkaloids The Quinazolinocarboline Alkaloids Vol. 21 1983 Academic Press New York 29 54
25. C.L. King, Y.C. Kong, N.S. Wong, H.W. Yeung, H.H. Fong, and U. Sankawa J. Nat. Prod. 43 1980 577 582
26. W.S. Sheen, I.L. Tsai, C.L. Teng, F.N. Ko, and I.S. Chen Planta Med. 62 1996 175 176
27. G.J. Wang, J. Shan, P.K.T. Pang, M.C.M. Yang, C.J. Chou, and C.F. Chen J. Pharmacol. Exp. Therap. 270 1996 1016 1021
28. S.-N. Wu, Y.-K. Lo, H. Chen, H.-F. Li, and H.-T. Chiang Neuropharmacology 41 2001 834 843
29. W.F. Chiou, C.J. Chou, J.F. Liao, A.Y. Sham, and C.F. Chen Eur. J. Pharmacol. 257 1994 59 66
30. W.F. Wang, C.J. Wu, C.F. Chen, L.C. Lin, Y.T. Huan, J. Shan, and P. Pang J. Pharmacol. Exp. Ther. 289 1999 1237 1244
31. C.-P. Hu, L. Xiao, H.-W. Deng, and Y.-J. Li Planta Med. 68 2002 705 709
32. C.-P. Hu, L. Xiao, H.-W. Deng, and Y.-J. Li Planta Med. 69 2003 125 129
33. M.-J. Don, D.F.V. Lewis, S.-Y. Wang, M.-W. Tsai, and Y.-F. Ueng Bioorg. Med. Chem. Lett. 13 2003 2535 2538
34. H. Itokawa, M. Inamatsu, and K. Takeya Shouyakugaku Zasshi 44 1990 135 137
35. L.-M. Yang, C.-F. Chen, and K.-H. Lee Bioorg. Med. Chem. Lett. 5 1995 465 468
36. L.M. Yang, S.-J. Lin, L.-C. Lin, and Y.-H. Kuo Chin. Pharm. J. 51 1999 219 225
37. J. Kökösi, I. Hermecz, G. Szasz, and Z. Měszaros Tetrahedron Lett. 22 1981 4861 4862
38. J. Kökösi, G. Szasz, and I. Hermecz Tetrahedron Lett. 33 1992 2995 2998
39. S.H. Lee, S.I. Kim, J.G. Park, E.S. Lee, and Y. Jahng Heterocycles 55 2001 1555 1560
40. H.W. Chang, S.I. Kim, H. Jung, and Y. Jahng Heterocycles 60 2003 1359 1366
41. S.P. Chavan, and R. Sivappa Tetrahedron Lett. 45 2004 997 999
42. S.B. Mhaske, and N.P. Argade Tetrahedron 60 2004 3417 3420
43. E.S. Lee, J.-G. Park, and Y. Jahng Tetrahedron Lett. 44 2003 1883 1886
44. B. Baruah, K. Dasu, B. Vaitilingam, P. Mamnoor, P.P. Venkata, S. Rajagopal, and K.R. Yeleswarapu Bioorg. Med. Chem. 12 2004 1991 1994
45. M.-F. Pereira, L. Picot, J. Guillon, J.-M. Léger, C.R. Jarry, V. Thiéry, and T. Besson Tetrahedron Lett. 46 2005 3445 3447
46. T. Kametani, T. Higa, C. Von Loc, M. Ihara, M. Koizumi, and K. Fukumoto J. Am. Chem. Soc. 98 1976 6186 6188
47. T. Kametani, C. Von Loc, T. Higa, M. Koizumi, M. Ihara, and K. Fukumoto J. Am. Chem. Soc. 99 1977 2306 2309
48. J. Bergman, and S. Bergman J. Org. Chem. 50 1985 1246 1255
49. P.K. Mohanta, and K. Kim Tetrahedron Lett. 43 2002 3993 3996
50. T. Harayama, A. Hori, G. Serban, Y. Morikami, T. Matsumoto, H. Abe, and Y. Takeuchi Tetrahedron 60 2004 10645 10649
51. For the synthesis of the triheterocyclic thiolactam 4, see: P. Benovskyf, and J.R. Stille Tetrahedron Lett. 38 1997 8475 8478
52. M.W. Gittos, M.R. Robinson, J.P. Verge, R.V. Davies, B. Iddon, and H. Suschitzky J. Chem. Soc., Perkin Trans. 1 1976 33 38
53. For heteroannulation using this concept and leading to imidazolo-, thiazolo-, and thiazinopyrimidones, see: F. Sauter, J. Fröhlich, K. Blasl, and K. Gewald Heterocycles 40 1995 851 866
54. F. Sauter, J. Fröhlich, A.Z.M.S. Chowdhury, and C. Hametner Monatsh.Chem. 128 1997 503 508
55. F. Sauter, J. Fröhlich, A.Z.M.S. Chowdhury, and C. Hametner Sci. Pharm. 65 1997 83 85
56. F.-R. Alexandre, A. Berecibar, R. Wrigglesworth, and T. Besson Tetrahedron 59 2003 1413 1419
57. M.G. Bock, R.M. DiPardo, S.M. Pitzenberger, C.F. Homnick, J.P. Springer, and R.M. Freidinger J. Org. Chem. 52 1987 1646 1647
58. See also the use of this protocol in dihydro-isoquinoline series: Y.V. Shklyaev, V.A. Glushkov, N.B. Belogub, and N.B. Misyura Chem. Heterocycl. Compd. 32 1996 689 695
59. 3O: C, 67.19; H, 3.76; N, 13.06. Found: C, 67.03; H, 3.54; N, 12.96.
60. 2: C, 71.46; H, 5.37; N, 13.16. Found: C, 71.31; H, 5.21; N, 13.09.
61. M. Perrisin, D.C. Luu, G. Narcisse, F. Bakri-Logeais, and F. Huguet J. Med. Chem. Chim. Ther. 15 1980 563 565
62. See, for example, the following reference: P.C. Unangst J. Heterocycl. Chem. 20 1983 495 499
63. S.S. Sangapure, and Y.S. Agasimundin Ind. J. Chem. 14B 1976 686 691
64. H.D.H. Showalter, A.J. Bridges, H. Zhou, A.D. Sercel, A. McMichael, and D.W. Fry J. Med. Chem. Ch. 42 1999 5464 5474
65. S.W. Schneller, and F.W. Clough J. Heterocycl. Chem. 11 1974 975 977
66. 2; in our case we used a combination AcOH/Zn as a cheaper reagent for this purpose.
67. J.-F. Liu, P. Ye, K. Sprague, K. Sargent, D. Yohannes, C.M. Baldino, C.J. Wilson, and S.-C. Ng Org. Lett. 7 2005 3363 3366 and references cited therein