Chemistry of domoic acid, isodomoic acids, and their analogues

Tetrahedron

Volumn 61, Issue 24, 2005, Pages 5713-5724

  Clayden, Jonathan ^a   Read, Benjamin ^a   Hebditch, Katherine R ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

Domoic acid; Isodomoic acids; Marine alga

Indexed keywords

ALKENE DERIVATIVE; DOMOIC ACID; DOMOILACTONE A; DOMOILACTONE B; ISODOMOIC ACID; ISODOMOIC ACID A; ISODOMOIC ACID B; ISODOMOIC ACID C; ISODOMOIC ACID D; ISODOMOIC ACID E; ISODOMOIC ACID F; ISODOMOIC ACID G; ISODOMOIC ACID H; KAINIC ACID; LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CRYSTAL STRUCTURE; CRYSTALLIZATION; CYCLIZATION; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PRIORITY JOURNAL;

ALGAE;

EID: 19744375818     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.04.003     Document Type: Review

References (125)

1. S. Murakami, T. Takemoto, and Z. Shimizu J. Pharm. Soc. Jpn. 73 1953 1026
2. M. Maeda, T. Kodama, T. Tanaka, H. Yoshizumi, T. Takemoto, K. Nomoto, and T. Fujita Tetrahedron Lett. 28 1987 633
3. (a)Acromelic acids A and B: K. Konno, H. Shirahama, and T. Matsumoto Tetrahedron Lett. 24 1983 939
4. (b) Acromelic acid C: S. Fushiya, S. Sato, T. Kanazawa, G. Kusano, and S. Nozoe Tetrahedron Lett. 31 1990 3901
5. (c) Acromelic acids D and E: S. Fushiya, S. Sato, Y. Kera, and S. Nozoe Heterocycles 34 1992 1277
6. For a general review of the kainoid amino acids, see: A.F. Parsons Tetrahedron 52 1996 4149
7. T. Takemoto, and K. Daigo Chem. Pharm. Bull. 6 1958 578
8. K. Daigo J. Pharm. Soc. Jpn. 79 1959 350
9. (a) Isodomoic acids A to C: M. Maeda, T. Kodama, T. Tanaka, H. Yoshizumi, T. Takemoto, K. Nomoto, and T. Fujita Chem. Pharm. Bull. 34 1986 4892
10. (b) Isodomoic acid D: M. Maeda, T. Kodama, T. Tanaka, H. Yoshizumi, T. Takemoto, K. Nomoto, and T. Fujita Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 27 1985 616
11. M.A. Quilliam, P.G. Sim, A.W. McCulloch, and A.G. McInnes Int. J. Env. Anal. Chem. 36 1989 139
12. P. Vale, and M.A.de M. Sampayo Harmful Algae 1 2002 127
13. N. Pineiro, E. Vaquero, J.M. Leao, A. Gago-Martinez, and J.A.R. Vazquez Chromatographia 53 2001 231
14. S.W. Hadley, S.K. Braun, and M.M. Wekell F. Shahidi Y. Jones D.D. Kitts Seafood safety, processing and biotechnology 1997 Technomic Lancaster 25
15. J.Y. Zhao, P. Thibault, and M.A. Quilliam Electrophoresis 18 1997 268
16. J.A. Walter, M. Falk, A.G. McInnes, and J.L.C. Wright Can. J. Chem. 68 1990 22
17. L. Zaman, O. Arakawa, A. Shimosu, Y. Onoue, S. Nishio, Y. Shida, and T. Noguchi Toxicon 35 1997 205
18. For a detailed account of the process of discovery of domoic acid-producing organisms and an explanation of taxonomy, see (a) N. Lundholm, Ø. Moestrup, G.R. Hasle, and K. Hoef-Emden J. Phycol. 39 2003 797
19. S.S. Bates J. Phycol. 36 2000 978
20. S.S. Bates, C.J. Bird, A.S.W. De Freitas, R. Foxall, M. Gilgan, L.A. Hanic, G.R. Johnson, A.W. McCulloch, and P. Odense Can. J. Fish. Aquat. Sci. 46 1989 1203
21. D.J. Douglas, and S.S. Bates Can. J. Fish. Aquat. Sci. 49 1992 85
22. J.L. Martin, K. Haya, L.E. Burridge, and D.J. Wildish Mar. Ecol.: Prog. Ser. 67 1990 177
23. D.L. Garrison, S.M. Conrad, P.P. Eilers, and E.M. Waldron J. Phycol. 28 1992 604
24. L. Rhodes, D. White, M. Syhre, and M. Atkinson Y. Oshima Y. Fukuyo T. Yasumoto Harmful and toxic algal blooms 1996 Intergovernmental Oceanographic Commission, UNESCO Paris 155
25. D. Sarno, and J. Dahlmann Harmful Algae News 21 2000 5
26. N. Lundholm, Ø. Moestrup, J. Skov, and R. Pocklington Phycologia 33 1994 475
27. L. Rhodes, C. Scholin, I. Garthwaite, A. Haywood, and A. Thomas B. Reguera J. Blanco M.L. Fernández T. Wyatt Harmful algae 1998 Intergovernmental Oceanographic Commission, UNESCO Paris 274
28. For a detailed review of the role of domoic acid as a marine toxin, see L. Mos Environ. Toxicol. Pharmacol. 9 2001 79 and references therein
29. M. Maeda, T. Kodama, T. Tanaka, Y. Ohfune, K. Nishimura, K. Nomoto, and T. Fujita J. Pestic. Sci. 9 1984 27
30. H. Watase, Y. Tomiie, and I. Nitta Nature (London) 181 1958 761
31. S. Husinec, A.E.A. Porter, J.S. Roberts, and C.H. Strachan J. Chem. Soc., Perkin Trans. 1 1984 2517
32. E.G. McGeer J.W. Olney P.L. McGeer Kainic acid as a tool in neurobiology 1978 Raven New York
33. R.P. Simon Excitatory amino acids 1992 Thieme Medical New York
34. H.V. Wheal A.M. Thomson Excitatory amino acids and synaptic transmission 1991 Academic London
35. J.C. Watkins, P. Krogsgaard-Larsen, and T. Honoré Trends Pharmacol. Sci. 11 1990 25
36. R.H. Waring, G.B. Steventon, and S.C. Mitchell Molecules of death 2002 Imperial College London
37. G. Sperk Prog. Neurobiol. (Oxford) 42 1994 1
38. J.T. Coyle, and R. Schwarcz Nature (London) 263 1976 244
39. E.G. McGeer, and P.L. McGeer Nature (London) 263 1976 517
40. G.A.R. Johnson, D.R. Curtis, J. Davis, and R.M. McCulloch Nature (London) 248 1974 804
41. J.J. Hansen, and P. Krogsgaard-Larsen Med. Res. Rev. 10 1990 55
42. M. Ishida, and H. Shinozaki Br. J. Pharmacol. 104 1991 873
43. K. Hashimoto, Y. Ohfune, and H. Shirahama Tetrahedron Lett. 36 1995 6235
44. D.T. Monaghan, R.J. Bridges, and C.W. Cotman Annu. Rev. Pharmacol. Toxicol. 29 1989 365
45. A.B. Young, and G.E. Fagg Trends Pharmacol. Sci. 11 1990 126
46. B. Sommer, and P.H. Seeburg Trends Pharmacol. Sci. 13 1992 291
47. P.H. Seeberg Trends Neurosci. 16 1993 359
48. M. Hollmann, and S. Heinemann Annu. Rev. Neurosci. 17 1994 31
49. D.R. Hampson, X. Huang, J.W. Wells, J.A. Walter, and J.L.C. Wright Eur. J. Pharmacol. 218 1992 1
50. S.S. Bates, C.J. Bird, A.S.W. De Freitas, R. Foxall, M. Gilgan, L.A. Hanic, G.R. Johnson, A.W. McCulloch, and P. Odense Can. J. Fish. Aquat. Sci. 46 1989 1203
51. J.L.C. Wright, R.K. Boyd, A.S.W. De Freitas, M. Falk, R.A. Foxall, W.D. Jamieson, M.V. Laycock, A.W. McCulloch, and A.G. McInnes Can. J. Chem. 67 1989 481
52. C.A. Scholin, F. Gulland, G.J. Doucette, S. Benson, M. Busman, F.P. Chavez, J. Cordar, R. DeLong, A. De Vogelaere, J. Harvey, M. Haulena, K. Lefebvre, T. Lipscomb, S. Loscutoff, L.J. Lowenstine, R.I. Martin, P.E. Miller, W.A. McLellan, P.D.R. Moeller, C.L. Powell, T. Rowles, P. Silvagni, M. Silver, T. Spraker, V. Trainer, and F.M. Van Dolah Nature 403 2000 80
53. T.M. Work, A.M. Beale, L. Fritz, M.A. Quilliam, M. Silver, K. Buck, and J.L.C. Wright T.J. Smayda Y. Shimizu Toxic phytoplankton blooms in the sea 1993 Elsevier Science Amsterdam 643
54. A. Sierra-Beltrán, M. Palafox-Uribe, J. Grajales-Montiel, A. Cruz-Villacorta, and J.L. Ocha Toxicon 35 1997 447
55. J. Fehling, D.H. Green, K. Davidson, C.J. Bolch, and S.S. Bates J. Phycol. 40 2004 622
56. C.K. Cusack, S.S. Bates, M.A. Quilliam, J.W. Patching, and R. Raine J. Phycol. 38 2002 1106
57. M.C. Villac, D.L. Roelke, T.A. Villareal, and G.A. Fryxell Hydrobiologia 269-270 1993 213
58. J.E. Stewart, L.J. Marks, M.W. Gilgan, E. Pfeiffer, and B.M. Zwicker Can. J. Microbiol. 44 1998 456
59. E.A. Smith, F. Grant, C.M.J. Ferguson, and S. Gallacher Appl. Environ. Microbiol. 67 2001 2345
60. Racemic syntheses: (a) J.C. Anderson, and M. Whiting J. Org. Chem. 68 2003 6160
61. S.-E. Yoo, S.-H. Lee, K.-Y. Yi, and N. Jeong Tetrahedron Lett. 31 1990 6877
62. M.D. Bachi, N. Bar-Ner, and A. Melman J. Org. Chem. 61 1996 7116
63. M.D. Bachi, and A. Melman Synlett 1996 60
64. J. Clayden, and K. Tchabanenko Chem. Commun. 2000 317
65. Asymmetric syntheses: (f) H. Hirasawa, T. Taniguchi, and K. Ogasawara Tetrahedron Lett. 42 2001 7587
66. O. Miyata, Y. Ozawa, I. Ninomiya, and T. Naito Tetrahedron 56 2000 6199
67. A.D. Cambell, T.M. Raynham, and R.J.K. Taylor J. Chem. Soc., Perkin Trans. 1 2000 3194
68. M.V. Chevliakov, and J. Montgomery J. Am. Chem. Soc. 121 1999 11139
69. A. Rubio, J. Ezquerra, A. Escribano, J. Modesto, M.J. Remuiñán, and J.J. Vanquero Tetrahedron Lett. 39 1998 2171
70. J. Cossy, M. Cases, and D.G. Pardo Synlett 1998 507
71. M.D. Bachi, and A. Melman J. Org. Chem. 62 1997 1896
72. J. Cooper, D.W. Knight, and P.T. Gallagher J. Chem. Soc., Chem. Commun. 1987 1220
73. W. Oppolzer, and K. Thirring J. Am. Chem. Soc. 104 1982 4978
74. J. Cooper, D.W. Knight, and P.T. Gallagher J. Chem. Soc., Perkin Trans. 1 1992 553
75. S. Takano, Y. Iwabuchi, and K. Ogasawara J. Chem. Soc., Chem. Commun. 1988 1204
76. S. Takano, T. Sugihara, S. Satoh, and K. Ogasawara J. Am. Chem. Soc. 110 1988 6467
77. S.-E. Yoo, S.-H. Lee, N. Jeong, and I. Cho Tetrahedron Lett. 34 1993 3435
78. S.-E. Yoo, and S.-H. Lee J. Org. Chem. 59 1994 6968
79. S. Takano, K. Inomata, and K. Ogasawara J. Chem. Soc., Chem. Commun. 1992 169
80. A. Barco, S. Benetti, G.P. Pollini, G. Spalluto, and V. Zanirato J. Chem. Soc., Chem. Commun. 1991 390
81. S. Hatakeyama, K. Sugawara, and S. Takano J. Chem. Soc., Chem. Commun. 1993 125
82. S. Hanessian, and S. Ninkovic J. Org. Chem. 61 1996 5418
83. Y. Nakada, T. Sugahara, and K. Ogasawara Tetrahedron Lett. 38 1997 857
84. O. Miyata, Y. Ozawa, I. Ninomiya, and T. Naito Synlett 1997 275
85. J.A. Monn, and M.J. Valli J. Org. Chem. 59 1994 2773
86. B.M. Trost, and M.T. Rudd Org. Lett. 5 2003 1467
87. A.D. Campbell, T.M. Raynham, and R.J.K. Taylor Chem. Commun. 1999 245
88. Q. Xia, and B. Ganem Organic Lett. 3 2001 485
89. J. Clayden, C.J. Menet, and K. Tchabanenko Tetrahedron 58 2002 4727
90. J. Clayden, C.J. Menet, and D.J. Mansfield Chem. Commun. 2002 38
91. H. Nakagawa, T. Sugahara, and K. Ogasawara Org. Lett. 2 2000 3181
92. M. Kawamura, and K. Ogasawara Heterocycles 44 1997 129
93. J. Cossy, M. Cases, and D.G. Pardo Tetrahedron 55 1999 6153
94. J.E. Baldwin, M.G. Moloney, and A.F. Parsons Tetrahedron 46 1990 7263
95. Y. Ohfune, and M. Tomita J. Am. Chem. Soc. 104 1982 3511
96. R. Hoffmann, and R.B. Woodward The conservation of orbital symmetry 1970 Academic New York
97. J.L.C. Wright, R.K. Boyd, A.S.W. De Freitas, M. Falk, R.A. Foxall, W.D. Jamieson, M.V. Laycock, A.W. McCulloch, A.G. McInnes, P. Odense, V.P. Pathak, M.A. Quilliam, M.A. Ragan, P.G. Sim, P. Thibault, J.A. Walter, M. Gilgan, D.J.A. Richard, and D. Dewar Can. J. Chem. 67 1989 481
98. G.A. Conway, J.S. Park, L. Maggiora, M.P. Mertes, N. Galton, and E.K. Michaelis J. Med. Chem. 27 1984 52
99. N. Yike, K.D. Amarasinghe, B. Ksebati, and J. Montgomery Org. Lett. 5 2003 3771
100. For related observations, see: (a) H.-J. Breternitz, E. Schaumann, and G. Adiwidjaja Tetrahedron Lett. 32 1991 1299
101. D. Hoell, J. Lex, and K. Müllen J. Am. Chem. Soc. 108 1986 5983
102. A. Padwa, M.A. Filipkowski, D.N. Kline, S.S. Murphree, and P.E. Yeske J. Org. Chem. 58 1993 2061
103. J.K. Crandall, and T.A. Ayers J. Org. Chem. 67 2002 2335
104. J. Clayden, and M.N. Kenworthy Synthesis 2004 1721
105. J. Clayden Organolithiums: selectivity for synthesis 2002 Pergamon New York pp 327-329
106. Jaeger, S. Ph.D. Thesis, University of Manchester, 1996.
107. Beech, C. Final Year Undergraduate Project, University of Manchester, 1995.
108. A. Ahmed, J. Clayden, and M. Rowley Chem. Commun. 1998 297
109. A. Ahmed, J. Clayden, and S.A. Yasin Chem. Commun. 1999 231
110. For a review, see: J. Clayden Total synthesis of kainoids by dearomatizing cyclization M. Harmata Strategies and tactics in organic synthesis Vol. 4 2004 Academic New York 72 96
111. J. Clayden, C.J. Menet, and D. Mansfield Org. Lett. 26 2000 4229
112. J. Clayden, K. Tchabanenko, S.A. Yasin, and M.D. Turnbull Synlett 2001 302
113. C. Metallinos, S. Nerdinger, and V. Snieckus Org. Lett. 1 1999 1183
114. G.H. Posner, Q. Wang, B.A. Halford, J.S. Elias, and J.P. Maxwell Tetrahedron Lett. 41 2000 9655
115. K. Nakatani, and S. Isoe Tetrahedron Lett. 25 1984 5335
116. J.E. Baldwin, R.M. Adlington, and J. Robertson J. Chem. Soc., Chem. Commun. 1988 1404
117. J.E. Baldwin, M.G. Moloney, and A.F. Parsons Tetrahedron 47 1991 155
118. J.E. Baldwin, G.J. Pritchard, and D.S. Williamson Bioorg. Med. Chem. Lett. 10 2000 1927
119. J.E. Baldwin, G.J. Pritchard, and D.S. Williamson Tetrahedron 57 2001 7991
120. J.E. Baldwin, G.J. Pritchard, and A.M. Fryer J. Org. Chem. 66 2001 2588
121. J.E. Baldwin, G.J. Pritchard, and A.M. Fryer Bioorg. Med. Chem. Lett. 10 2000 309
122. J.E. Baldwin, M.R. Spyvee, R.C. Whitehead, M.E. Wood, and A.M. Fryer Tetrahedron 53 1997 5273
123. J.E. Baldwin, S.J. Bamford, M.P.W. Rudolph, M.E. Wood, and A.M. Fryer Tetrahedron 53 1997 5255
124. J.E. Baldwin, S.J. Bamford, M.P.W. Rudolph, M.E. Wood, and A.M. Fryer Tetrahedron 53 1997 5233
125. J.E. Baldwin, A.M. Fryer, M.R. Spyvee, R.C. Whitehead, and M.E. Wood Tetrahedron Lett. 37 1996 6923