Synthetic approaches to the eudistomin marine alkaloids

Current Organic Chemistry

Volumn 4, Issue 2, 2000, Pages 121-138

  McNulty, J ^a   Still, I W J ^b  

^a BROCK UNIVERSITY   (Canada)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BETA CARBOLINE; CALCIUM; CYSTEINE; DRUG METABOLITE; EUDISTOMIN DERIVATIVE; GLUTAMIC ACID; NATURAL PRODUCT; PHENYLALANINE DERIVATIVE; PHOSPHODIESTERASE; PROLINE DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ANTIVIRAL ACTIVITY; BACTERIAL INFECTION; CANCER; DRUG ACTIVITY; DRUG DETERMINATION; DRUG ISOLATION; DRUG SYNTHESIS; REVIEW; STRUCTURE ANALYSIS; VIRUS INFECTION;

EID: 0034129384     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272003376319     Document Type: Review

References (91)

1. Faulkner, D.J. Nat. Prod. Rep., 1998, 15, 113 and previous reports in this series. For an interesting earlier review see: Faulkner, D.J. Tetrahedron, Tetrahedron Report No. 28, 1977, 33, 1421.
2. Faulkner, D.J. Nat. Prod. Rep., 1998, 15, 113 and previous reports in this series. For an interesting earlier review see: Faulkner, D.J. Tetrahedron, Tetrahedron Report No. 28, 1977, 33, 1421.
3. Gribble, G.W. Acc. Chem. Res., 1998, 31, 141.
4. Pettit, G.R. J. Nat Prod., 1996, 59, 812.
5. Rinehart, K.L.; Kobayashi, J.; Harbour, G.C.; Hughes, R.G.; Mizsak, S.A.; Scahill, T.A. J. Am. Chem. Soc., 1984, 106, 1524.
6. Kobayashi, J.; Harbour, G.C.; Gilmore, J.; Rinehart, K.L, J. Am. Chem. Soc., 1984, 106, 1526.
7. Rinehart, K.L.; Kobayashi, J.; Harbour, G.C.; Gilmore, J.; Mascal, M.; Holt, T.G.; Shield, L.S.; Lafargue, F. J. Am. Chem. Soc., 1987, 109, 3378.
8. Kinzer, K.F.; Cardellina, J.H. Tetrahedron Lett., 1987, 28, 925.
9. Kobayashi, J.; Nakamura, H.; Ohizumi, Y.; Hirata, Y. Tetrahedron Lett., 1986, 27, 1191.
10. Kobayashi, J.; Cheng, J.; Ohta, T.; Nozoe, S.; Ohizumi, Y.; Sasaki, T. J. Org. Chem., 1990, 55, 3666.
11. Murata, O.; Shlgemori, H.; Ishibashi, M.; Sugama, K.; Hayashi, K.; Kobayashi, J. Tetrahedron Lett., 1991, 32, 3539.
12. Lake, R.J.; Brennan, M.M.; Blunt, J.W.; Munro, M.H.G. Tetrahedron Lett., 1988, 39, 2255.
13. Lake, R.J.; Blunt, J.W.; Munro, M.H.G. Aust. J. Chem., 1989, 42, 1201.
14. Debitus, C.; Laurent, D.; Païs, M. J. Nat. Prod., 1988, 51, 799.
15. Davis, R.A.; Carroll, A.R.; Quinn, R.J. J. Nat. Prod., 1998, 61, 959.
16. Adesanya, S.A.; Chbani, M.; Païs, M. Debitus, C. J. Nat. Prod., 1992, 55, 525.
17. Badre, A.; Boulanger, A.; Abou-Mansour, E.; Banaigs, B.; Combaut, G.; Francisco, C. J. Nat. Prod., 1994, 57, 528. Note structure revision; see [85] and Kang, H.; Fenical, W. Nat. Prod. Lett., 1996, 9,7.
18. Badre, A.; Boulanger, A.; Abou-Mansour, E.; Banaigs, B.; Combaut, G.; Francisco, C. J. Nat. Prod., 1994, 57, 528. Note structure revision; see [85] and Kang, H.; Fenical, W. Nat. Prod. Lett., 1996, 9,7.
19. Guella, G.; Mancini, I.; Duhet, D.; Richer de Forges, B.; Pietra, F. Z. Naturforsch., 1989, 44c, 914.
20. Kondo, K.; Shigemori, H.; Kikuchi, Y.; Ishibashi, M.; Sasaki, T.; Kobayashi, J. J. Org. Chem., 1992, 57, 2480.
21. Rudi, A.; Kashman, Y. J. Org. Chem., 1989, 54, 5331.
22. Kobayashi, J.; Cheng, J.; Kikuchi, Y.; Ishibashi, M.; Yamamura, S.; Ohizumi, Y.; Ohta, T.; Nozoe, S. Tetrahedron Lett., 1990, 31, 4617.
23. He, H.; Faulkner, D.J. J. Org. Chem., 1991, 56, 5369.
24. Makarieva, T.N.; Ilyin, S.G.; Stonik, V.A.; Lyssenko, K.A.; Denisenko, V.A. Tetrahedron Lett., 1999, 40, 1591.
25. Kikuchl, Y.; Ishibashi, M.; Sasaki, T.; Kobayashi, J. Tetrahedron Lett., 1991, 32, 797.
26. Van Wagoner, R.M.; Jompa, J.; Tahir, A.; Ireland, C.M. J. Nat. Prod., 1999, 62, 794.
27. Shen, G.Q.; Baker, B.J. Tetrahedron Lett., 1994, 35, 1141.
28. Shen, G.Q.; Baker, B.J. Tetrahedron Lett., 1994, 35, 4923.
29. VanWagenen, B.C.; Cardellina, J.H. Tetrahedron Lett., 1989, 30, 3605.
30. Kobayashi, J.; Taniguchi, M.; Hino, T.; Ohizumi, Y. J. Pharm. Pharmacol., 1988, 40, 62.
31. Kobayashi, J.; Ishibashi, M.; Nagai, U.; Ohizumi, Y. Experientia, 1989, 45,782.
32. Nakamura, Y.; Kobayashi, J.; Gilmore, J.; Mascal, M.; Rinehart, K.L.; Nakamura, H.; Ohizumi, Y. J. Biol. Chem., 1986, 261(9), 4139.
33. The chemical equivalent of this process is known: Ho, B.T.; Walker, K.E. Org. Synth., 1971, 51, 136.
34. Harrigan, G.C.; Luesch, H.; Yoshida, W.Y.; Moore, R.E.; Nagle, D.G.; Paul, V.J. J. Nat. Prod., 1999, 62, 655.
35. Schumacher, R.W.; Davidson, B.S. Tetrahedron, 1995, 51, 10125.
36. Bourguet-Kondracki, M.L.; Martin, M.T.; Guyot, M. Tetrahedron Lett., 1996, 37, 3457.
37. Kobayashi, M.; Chen, Y.J.; Aoki, S.; In, Y.; Ishida, T.; Kitagawa, I. Tetrahedron, 1995, 51, 3723.
38. Horiuchi, K.; Yonekawa, O.; Iwahara, K.; Kanno, T.; Kurihara, T.; Fujise, Y. J. Biochem., 1994, 115, 362.
39. For a general listing of references see: Merck Index, 12th Ed., Merck and Co, Whitehouse Station, N.J., 1996, monographs 4646 and 4647.
40. Wu, F.E.; Koike, K.; Nikaido, T.; Sakamoto, Y.; Ohmoto, T.; Ikeda, K. Chem. Pharm. Bull., 1989, 37, 1808.
41. Zhou, T.S.; Ye, W.C.; Wang, Z.T.; Che, C.T.; Zhou, R.H.; Xu, G.J.; Xu, L.S. Phytochem., 1998, 49, 1807.
42. Julian, P.L.; Karpel, W.J.; Magnani, A.; Meyer, E.W. J. Am. Chem. Soc., 1948, 70, 180. For a review of non-monoterpenoid indole alkaloids see: Ihara, M.; Fukumoto, K. Nat. Prod. Rep., 1997, 14, 413 and previous reports in this series.
43. Julian, P.L.; Karpel, W.J.; Magnani, A.; Meyer, E.W. J. Am. Chem. Soc., 1948, 70, 180. For a review of non-monoterpenoid indole alkaloids see: Ihara, M.; Fukumoto, K. Nat. Prod. Rep., 1997, 14, 413 and previous reports in this series.
44. Davidson, B.S. Chem. Rev. 1993, 93, 1771.
45. Wrobel, J.T.; Wojtasiewicz, K. In The Alkaloids; G.A. Cordell, Ed.; Academic Press, Inc.: San Diego, CA, 1992; Vol. 42, pp. 250-297.
46. Love, B.E. Org. Prep. Proced. Int., 1996, 28, 1.
47. Cox, E.D.; Cook, J.M. Chem. Rev. 1995, 95, 1797.
48. Hino, T.; Nakagawa, M. Heterocycles, 1998, 49, 499.
49. Han, S.-Y.; Lakshmikantham, M.V.; Cava, M.P. Heterocycles, 1985, 23, 1671.
50. Hino, T.; Hasegawa, A.; Liu, J.-J.; Nakagawa, M. Chem. Pharm. Bull., 1990, 38, 59.
51. Sandrin, J.; Hollinshead, S.P.; Cook, J.M. J. Org. Chem. 1989, 54, 5636.
52. Waldmann, H.; Schmidt, G.; Henke, H.; Burkard, M. Angew. Chem. Int. Ed. Engl., 1995, 34, 2402.
53. Soe, T.; Kawate, T.; Fukui, N.; Hino, T.; Nakagawa, M. Heterocycles, 1996, 42, 347.
54. Kawate, T.; Yamada, H.; Soe, T.; Nakagawa, M. Tetrahedron: Asymmetry, 1996, 7, 1249.
55. Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc., 1994, 118, 10520.
56. Liu, J.-J.; Nakagawa, M.; Hino, T. Tetrahedron, 1989, 45, 7729.
57. Liu, J.-J.; Nakagawa, M.; Ogata, K.; Hino, T. Chem. Pharm. Bull. 1991, 39, 1672.
58. Hino, T.; Nakagawa, M. J. Heterocycl. Chem., 1994, 31, 625.
59. Nakagawa, M.; Liu, J.-J.; Hino, T. J. Am. Chem. Soc., 1989, 111, 2721.
60. Still, I.W.J.; Strautmanis, J. Can. J. Chem., 1990, 68, 1408.
61. Hermkens, P.H.H; van Maarseveen, J.H.; Ottenheijm, H.C.J.; Kruse, C.G.; Scheeren, H.W. J. Org. Chem., 1990, 55, 3998.
62. Hermkens, P.H.H; van Maarseveen, J.H.; Bevens, H.W.; Smits, J.M.; Kruse, C.G.; Soheeren, H.W. J. Org. Chem., 1990, 55, 2200.
63. Kirkup, M.P.; Shankar, B.B.; McCombie, S.; Ganguly, A.K.; McPhail, AT. Tetrahedron Lett., 1989, 30, 6809.
64. van Maarseveen, J.H.; Scheeren, H.W.; Kruse, C.G. Tetrahedron, 1993, 49, 2325.
65. van Maarseveen, J.H.; Oberye, E.H.H.; Bolster, M.B.; Scheeren, H.W.; Kruse, C.G. Recl. Trav. Chim. Pays-Bas, 1995, 114, 27.
66. van Maarseveen, J.H.; Scheeren, H.W.; Declercq, E.; Balzarini, J.; Kruse, C.G. Biorg. Med. Chem., 1997, 5, 955.
67. Kurihara, T.; Sakamoto, Y.; Kimura, T.; Ohishi, H.; Harusawa, S.; Yoneda, R.; Suzutani, T.; Azuma, M. Chem. Pharm. Bull., 1996, 44, 900.
68. Wasserman, H.H.; Kelly, T.A. Tetrahedron Lett., 1989, 30, 7117.
69. Molina, P.; Fresneda, P.M.; Canovas, M. Tetrahedron Lett., 1992, 33, 2891.
70. Hino, T.; Lai, Z.; Seki, H.; Hara, R.; Kuramochi, T.; Nakagawa, M. Chem. Pharm. Bull., 1989, 37, 2596.
71. Murakami, Y.; Takahashi, H.; Nakazawa, Y.; Koshimizu, M.; Watanabe, T.; Yokoyama, Y. Tetrahedron Lett., 1989, 30, 2099.
72. Murakami, Y.; Watanabe, T.; Takahashi, H.; Yokoo, H.; Nakazawa, Y.; Koshimizu, M.; Adachi, N.; Kurita, M.; Yoshino, T.; Inagaki, T.; Ohishi, M.; Watanabe, M.; Tani, M.; Yokoyama, Y. Tetrahedron, 1998, 54, 45.
73. McNulty, J; Still, I.W.J. Synth. Commun., 1992, 22, 979.
74. McNulty, J.; Still, I.W.J. Tetrahedron Lett., 1991, 32, 4875.
75. McNulty, J.; Still, I.W.J. J. Chem. Soc. Perkin Trans. 1, 1994, 1329.
76. Mahboobi, S. Arch. Pharm (Weinheim), 1992, 325, 249.
77. Bracher, F.; Hildebrand, D.; Ernst, L. Arch. Pharm. (Weinheim), 1994, 327, 121.
78. Still, I.W.J.; McNulty, J. Heterocycles, 1989, 29, 2057.
79. Molina, P.; Fresneda, P.M.; Garcia-Zafra, S. Tetrahedron Lett., 1996, 37, 9353.
80. Rocca, P.; Marsais, F.; Godard, A.; QuÇguiner, G.; Adams, L.; Alo, B. Synth. Commun., 1995, 25, 3373.
81. McNulty, J.; Still, I.W.J. Tetrahedron Lett., 1995, 36, 7965.
82. Polniaszek, R.P.; Bell, S.J. Tetrahedron Lett., 1996, 37, 575.
83. Ohta,T.; Somei, M. Heterocycles, 1989, 29, 1663.
84. Schumacher, R.W.; Davidson, B.S. Tetrahedron, 1999, 55, 935.
85. Snyder, H.R.; Hansch, C.H.; Katz, L.; Parmerter, S.M.; Spaeth, E.G. J. Am. Chem. Soc., 1948, 70, 219.
86. Iwaki, T.; Yasuhara, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1, 1999, 1505.
87. Rocca, P.; Marsais, F.; Godard, A.; Quçguiner, G.; Adams, L.; Alo, B. Tetrahedron Lett., 1995, 36, 7085.
88. Massiot, G.; Nazabadioko, S.; Bliard, C. J. Nat. Prod., 1995, 58, 1636.
89. Misztal, S.; Bielecka, Z.; Mokrosz, J.L. J. Chem. Soc., Perkin Trans. 1, 1991, 1871.
90. Mistzal, S.; Dukat, M.; Mokrosz J.L. J. Chem. Soc., Perkin Trans. 1, 1990, 2311.
91. Molina, P.; Fresneda, P.M.; Garcia-Zafra, S. Tetrahedron Lett., 1995, 36, 3581.