Manzamine alkaloids, syntheses and synthetic approaches

Tetrahedron

Volumn 54, Issue 23, 1998, Pages 6201-6258

  Magnier, Emmanuel ^a   Langlois, Yves ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; BETA CARBOLINE DERIVATIVE; MANZAMINE ALKALOID; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; CYCLIZATION; CYTOTOXICITY; DRUG CONFORMATION; DRUG ISOLATION; DRUG SYNTHESIS; PRIORITY JOURNAL; REVIEW; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0032482288     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00357-3     Document Type: Review

References (84)

1. 1) a. Baker, B. J. β-Carboline and Isoquinoline Akaloids from Marine Organisms, in Alkaloids : Chemical and Biological Perspectives, S. W. Pelletier Ed., Elsevier, Oxford, 1996; Vol. 10, Chap. 4, pp. 358-407 and references there in.
2. b. Andersen, R. J.; Van Soest, R. W. M.; Kong, F. 3-Alkylpiperidine Alkaloids Isolated from Marine Sponges in the Order of Haplosclerida, in Alkaloids : Chemical and Biologocal Perspectives, S. W. Pelletier Ed., Elsevier, Oxford, 1996; Vol. 10, Chap 3, pp. 302-355.
3. c. For a recent review about the structures and biogenesis of manzamines and related alkaloids, see : Tsuda, M.; Kobayashi, J. Heterocycles, 1997, 46, 765-794.
4. d. Kobayashi, J.; Tsuda, M. Journal of Synthetic Organic Chemistry of Japan 1997, 55, 1114-1123.
5. 2) Sakai, R.; Higa, T.; Jefford, C. W.; Bernardinelli, G. J. Am. Chem. Soc. 1986, 108, 6404-6405.
6. 3) Nakamura, H.; Deng, S.; Kobayashi, J.; Ohizumi, Y. Tetrahedron Letters, 1987, 28, 621-624.
7. 4) Sakai, R.; Kohmoto, S.; Higa, T.; Jefford, C. W.; Bernardinelli. Tetrahedron Letters, 1987, 28, 5493-5496.
8. 5) Ichiba, T.; Sakai, R.; Kohmoto, S.; Saucy, G.; Higa, T. Tetrahedron Letters, 1988, 29, 3083-3086.
9. 6) Kondo, K; Shigemori, H.; Kikuchi, Y.; Ishibashi, M.; Sazaki, T.; Kobayashi, J. J. Org. Chem. 1992, 57, 2480-2483.
10. 7) Baldwin, J. E.; Whitehead, R. C. Tetrahedron Letters, 1992, 33, 2059-2062.
11. 8) Rodriguez, J.; Peters, B. M.; Kurz, L.; Schatzman, R.C.; McCarley, D.; Lou, L.; Crews, P. J. Am. Chem. Soc. 1993, 115, 10436-10437.
12. 9) a. Kong, F.; Andersen, R. J.; Allen, T. M. Tetrahedron Letters, 1994, 35, 1643-1646.
13. b. Kong, F.; Andersen, R. J.; Allen, T. M. Tetrahedron , 1994, 50, 6137-6144.
14. 10) Kobayashi, J.; Tsuda, M.; Kawazaki, N.; Matsumoto, K.; Adashi, T. Tetrahedron Letters, 1994, 35, 4383-4386.
15. 11) Tsuda, M.; Kawazaki, N.; Kobayashi, J. Tetrahedron Letters, 1994, 35, 4387-4388.
16. 12) Rodriguez, J.; Crews, P. Tetrahedron Letters, 1994, 35, 4719-4722.
17. 13) Crews, P.; Cheng, X.-C; Adamczeski, M.; Rodriguez, J.; Jaspar, M.; Schmitz, F. J.; Traeger, S. C.; Pordesimo, E. O. Tetrahedron, 1994, 50, 13567-13574.
18. 14) Jaspar, M.; Pasupathy,V.; Crews, P. J. Org. Chem. 1994, 59, 3253-3255.
19. 15) Ichiba, T.; Corgiat, J. M.; Scheuer, P. J.; Kelly-Borges M. J. Nat. Prod. 1994, 57, 168-170.
20. 16) Tsuda, M.; Kawazaki, N.; Kobayashi, J. Tetrahedron, 1994, 50, 7957-7960.
21. 17) Kobayashi, J.; Tsuda, M.; Kawazaki, N.; Szaki, T.; Mikami, Y. J. Nat. Prod. 1994, 57, 1737-1740.
22. 18) Kong, F.; Andersen, R. J. Tetrahedron, 1995, 51, 2895-2906.
23. 19) Kobayashi, M.; Chen, Y.-J.; Aoki, S.; In, Y.; Ishiba, T.; Kitagawa, I. Tetrahedron, 1995, 51, 3727-3736.
24. 20) Othani, I. I.; Ichiba, T.; Isobe, M.; Kelly-Borges, M.; Scheuer, P. J. Am. Chem. Soc. 1995, 117, 10743-10744.
25. 21) Tsuda, M.; Inaba, K.; Kawazaki, N.; Honma, K.; Kobayashi, J. Tetrahedron, 1996, 52, 2319-2324.
26. 22) Kobayashi, J.; Kawazaki, N.; Tsuda, M. Tetrahedron Letters, 1996, 37, 8203-8204.
27. 23) Edrada, R. A.; Proksch, Wray, V.; Witte, L.; Müller, W. E. G.; Van Soet, R. W. M. J. Nat. Prod. 1996, 59, 1056-1060.
28. 24) Bourguet-Kondracki, M. L.; Martin, M. T.; Guyot, M. Tetrahedron Letters, 1996, 37, 3457-3460.
29. 25) Kobayashi, J.; Watanabe, D.; Kawazaki, N.; Tsuda, M. J. Org. Chem. 1997, 62, 9236-9239.
30. 26) a. For biomimetic syntheses of terpenes and steroids, see : Heinemann, C.; Demuth, M. J. Am. Chem. Soc. 1997, 119, 1129-1130 and references there in.
31. b. For a recent example of a biomimetic synthesis of alkaloids see : Heathcock, C. H. Angew. Chem. Int. Ed. 1992, 31, 665-681.
32. c. For an example of biomimetic hemisynthesis of alkaloids, see : Langlois, N.; Guéritte, F.; Langlois, Y.; Potier, P. J. Am. Chem. Soc. 1976, 98, 7017-7024.
33. 27) a. Baldwin, J. E.; Claridge, T. D. W.; Heupel, F. A.; Whitehead, R. C. Tetrahedron Letters, 1994, 35, 7829-7832.
34. b. Baldwin, J. E.; Claridge, T. D. W.; Culshaw, A. J.; Heupel, F. A.; Smrckova, S.; Whitehead, R. C. Tetrahedron Letters, 1996, 37, 6919-6922.
35. c. Baldwin, J. E.; Bischoff, L.; Claridge, T. D. W.; Heupel, F. A.; Spring, D. R.; Whitehead, R. C. Tetrahedron , 1997, 53, 2271-2290.
36. 28) Grierson, D. S. Organic Reactions, 1990, 85-295.
37. 29) a. Gil, L.; Gateau-Olesker, A.; Marazano, C.; Das B. C. Tetrahedron Letters, 1995, 36, 707-710.
38. b. Gil, L.; Baucherel, X.; Martin, M.-T.; Marazano, C.; Das B. C. Tetrahedron Letters, 1995, 36, 6231-6234.
39. 30) Winkler, J. D.; Siegel, M. G.; Stelmach, J. E. Tetrahedron Letters, 1993, 34, 6509-6512.
40. 31) Winkler, J. D.; Stelmach, J. E.; Axten, J. Tetrahedron Letters, 1996, 37, 4317-4318.
41. 32) Winkler, J. D.; Stelmach, J. E.; Siegel, M. G.; Haddad, N.; Axten, J.; Daily III, W. P. Isr. J. Chem. 1997, 37, 47-67.
42. 33) Hart, D. J.; McKinney, J. A. Tetrahedron Letters, 1989, 30, 2611-2614.
43. 34) Campbell, J. A.; Hart, D. J. Tetrahedron Letters, 1992, 33, 6247-6250.
44. 35) Clark, J. S.; Hodgson, P. B. Tetrahedron Letters, 1995, 36, 2519-2522.
45. 36) Li, S.; Kosemura, S.; Yamamura, S. Tetrahedron Letters, 1994, 35, 8217-8220.
46. 37) Li, S.; Ohba, S.; Kosemura, S.; Yamamura, S. Tetrahedron Letters, 1996, 37, 7365-7368.
47. 38) Kamenecka, T. M.; Overman, L. E. Tetrahedron Letters, 1994, 35, 4279-4282.
48. 39) Romero, A. G.; Trost, B. M. J. Org. Chem. 1986, 51, 2332-2342.
49. 40) Audia, J. E.; Boisvert, L.; Patten, A. D.; Villalobos, A. Danishefsky, S. J. J. Org. Chem. 1989, 54, 3738-3740.
50. 41) de Oliviera Imbroisi, D.; Simpkins N. S. Tetrahedron Letters, 1989, 30, 4309-4312.
51. 42) de Oliviera Imbroisi, D.; Simpkins N. S. J. Chem. Soc. Perkin Trans I, 1991, 1815-1823.
52. 43) Nakagawa, M.; Lai, Z.; Torisawa, Y.; Hino, T. Heterocycles, 1990, 31, 999-1002.
53. 44) Torisawa, Y.; Nakagawa, M.; Takami, H.; Nagata, T.; Ayman, M.; Hino, T. Heterocydes, 1994, 39, 277-291.
54. 45) Torisawa, Y.; Nakagawa, M.; Arai, H.; Lai, Z.; Hino, T.; Nakata, T.; Oishi, T. Tetrahedron Letters, 1990, 31, 3195-3198.
55. 46) Torisawa, Y.; Nakagawa, M.; Hosaka, T.; Tanabe, K.; Lai, Z.; Ogata, K.; Nakata, T.; Oishi, T.; Hino, T. J. Org. Chem. 1992, 57, 5741-5747.
56. 47) Nakagawa, M.; Torisawa, Y.; Hosaka, T.; Tanabe, K.; Tavet, F.; Aikawa, M.; Hino, T. Heterocycles, 1993, 55, 1157-1170.
57. 48) Nakagawa, M.; Torisawa, Y.; Hosaka, T.; Tanabe, K.; Da-te, T.; Okamura, Hino, T. Tetrahedron Letters, 1993, 34, 4543-4546.
58. 49) Torisawa, Y.; Hosaka, T.; Tanabe, K.; Suzuki, N.; Motohashi, Y.; Hino, T.; Nakagawa, M. Tetrahedron, 1996, 52, 10597-10608.
59. 50) Torisawa, Y.; Motohashi, Y.; Ma, J.; Hino, T.; Nakagawa, M. Tetrahedron Letters, 1995, 36, 5579-5580.
60. 51) Ma, J.; Nakagawa, M.; Torisawa, Y.; Hino, T. Heterocycles, 1994, 38, 1609-1618.
61. 52) Magnier, E.; Langlois, Y. Tetrahedron Letters, 1995, 36, 9475-9478.
62. 53) Magnier, E.; Langlois Y. Tetrahedron Letters, 1998, 39, 837-840.
63. 54) Sageot, O.; Monteux, D.; Langlois, Y.; Riche, C.; Chiaroni, A. Tetrahedron Letters, 1996, 37, 7019-7022.
64. 55) Chesney, A.; Marko, I. E. Synth. Commun. 1990, 20, 3167-3180.
65. 56) Chesney, A.; Marko, I. E. Synlett, 1992, 275-278.
66. 57) Marko, I. E.; Southern, J. M.; Adams, H. Tetrahedron Letters, 1992, 33, 4657-4660.
67. 58) Leonard, J.; Fearnley, S. P.; Hickey, D.M.B. Synlett, 1992, 272-274.
68. 59) Leonard, J.; Fearnley, S. P.; Finlay, M.R.; Knight, J.A.; Wong, G. J. Chem. Soc. Perkin Trans I, 1994, 2359-2361.
69. 60) Martin, S.F.; Rin, T.; Liao, Y. Tetrahedron Letters, 1991, 32, 6481-6484.
70. 61) Martin, S. F.; Liao, Y.; Wong, Y.; Rein, T. Tetrahedron Letters, 1994, 35, 691-694.
71. 62) Martin, S.F.; Chen, H.-J.; Courteny, A. K.; Liao, Y.; Pätzel, M.; Ramser, M.N.; Wagman, A.S. Tetrahedron, 1996, 52, 7251-7264.
72. 63) Schuster, M.; Blechert, S. Angew. Chem. Int. Ed. 1997, 36, 2037-2056.
73. b) Schmalz, H.-G. Angew. Chem. Int. Ed;.1995, 34, 1833-1836.
74. 64) Brands, K.M.J.; Pandit, U. K. Tetrahedron Letters, 1989, 30, 1423-1426.
75. 65) Brands, K.M.J.; Pandit, U. K. Heterocycles, 1990, 30, 257-261.
76. 66) Brands, K.M.J.; Meekel, A.A.P.; Pandit, U.K. Tetrahedron, 1991, 47, 2005-2026.
77. 67) Borer, B.C.; Deerenberg, S.; Bieräugel, H.; Pandit, U.K. Tetrahedron Letters, 1994, 35, 3191-3194.
78. 68) Pandit, U.K.; Borer, B.C.; Bieräugel, H, Pure & Appl. Chem. 1996, 68, 659-662.
79. 69) Pandit, U.K. J. Heterocyclic Chem. 1994, 31, 615-624.
80. 70) Pandit, U.K.; Borer, B.C.; Bieräugel, H.; Deerenberg, S. Pure & Appl. Chem. 1994, 66, 2131-2134.
81. 71) Torisawa, Y.; Hashimoto, A.; Nakagawa, M.; Seki, H.; Hara, R.; Hino, T. Tetrahedron, 1991, 47, 8067-8078.
82. 72) Nowak, W.; Gerlach, H. Liebigs Ann. Chem. 1993, 153-159.
83. 73) Torisawa, Y.; Hashimoto, A.; Okouchi, M.; Iimori, T.; Nagasawa, M.; Hino, T.; Nakagawa, M. Bioorg. Med.Chem.Lett. 1996, 6, 2565-2570.
84. Emmanuel Magnier was born in Rue in 1970. After his master's degree at the Université de Paris-Sud, he received the PhD degree working under the supervision of Professor Y. Langlois in 1997 on synthetic approaches of manzamine alkaloids. As the holder of a Bourse Lavoisier, he is currently working as a postdoctoral fellow with Professor W. B. Motherwell in University College London.