Synthesis of tetrodotoxin, a classic but still fascinating natural product

Chemical Record

Volumn 13, Issue 3, 2013, Pages 286-302

  Nishikawa, Toshio ^a   Isobe, Minoru ^b  

^a NAGOYA UNIVERSITY   (Japan)

^b NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

natural products; puffer fish; tetrodotoxin; total synthesis

Indexed keywords

BIOLOGICAL PRODUCT; CYCLOHEXANE; CYCLOHEXANE DERIVATIVE; GUANIDINE; LACTONE; TETRODOTOXIN;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLOADDITION; METABOLISM; STEREOISOMERISM; SYNTHESIS; TETRAODONTIFORMES;

ANIMALS; BIOLOGICAL PRODUCTS; CYCLOADDITION REACTION; CYCLOHEXANES; GUANIDINE; LACTONES; MODELS, MOLECULAR; STEREOISOMERISM; TETRAODONTIFORMES; TETRODOTOXIN;

EID: 84879148880     PISSN: 15278999     EISSN: 15280691     Source Type: Journal    
DOI: 10.1002/tcr.201200025     Document Type: Article

References (74)

1. a) Y. Tahara, J. Pharm. Soc. Jpn. 1909, 29, 587 (in Japanese)
2. b) Y. Tahara, Biochem. Z. 1911, 30, 255.
3. A. Yokoo, Proc. Jpn. Acad. 1952, 28, 200.
4. International Symposium on the Chemistry of Natural Products 1964 (Eds.: Organizing Committee of International Conference of Natural Products Chemistry, The Science Council of Japan), Tokyo Kagaku-Dojin, Tokyo, 1965.
5. a) T. Goto, Y. Kishi, S. Takahashi, Y. Hirata, Tetrahedron 1965, 21, 2059
6. b) K. Tsuda, S. Ikuma, M. Kawamura, R. Tachikawa, K. Sakai, C. Tamura, O. Amakasu, Chem. Pharm. Bull. 1964, 12, 1357
7. c) R. B. Woodward, Pure. Appl. Chem. 1964, 9, 49.
8. A. Furusaki, Y. Tomie, I. Nitta, Bull. Chem. Soc. Jpn. 1970, 43, 3325.
9. Review:, M. Yotsu-Yamashita, J. Toxicol., Toxin Rev. 2001, 20, 51.
10. M. Yotsu-Yamashita, A. Sugimoto, A. Takai, T. Yasumoto, J. Pharmacol. Exp. Ther. 1999, 289, 1688.
11. Bound structure by computer modeling:, D. B. Tikhonov, B. S. Zhorov, Biophys. J. 2005, 88, 184.
12. Reviews: a), U. Koert, Angew. Chem., Int. Ed. 2004, 43, 5572
13. b) J. Chau, M. A. Ciufolini, Mar. Drugs 2011, 9, 2046.
14. For leading references from other groups, see: a), B. A. Mendelsohn, M. A. Ciufolini, Org. Lett. 2009, 11, 4736
15. b) D. F. Taber, P. H. Storck, J. Org. Chem. 2003, 68, 7768
16. c) T. Itoh, M. Watanabe, T. Fukuyama, Synlett 2002, 1323
17. d) B. Noya, M. D. Paredes, L. Ozores, R. Alanso, J. Org. Chem. 2000, 65, 5960
18. e) B. Fraser-Reid, C. S. Burgey, R. Vollerthun, Pure Appl. Chem. 1998, 70, 285
19. f) R. J. Nachman, M. Hönel, T. M. Williams, R. C. Halaska, H. S. Mosher, J. Org. Chem. 1986, 51, 4802
20. g) J. F. Keana, J. S. Bland, P. J. Boyle, M. Erion, R. Harrtling, J. R. Husman, R. B. Roman, J. Org. Chem. 1983, 48, 3621
21. h) J. Speslacis, PhD thesis, Harvard University, 1975.
22. a) Y. Kishi, M. Aratani, T. Fukuyama, F. Nakatsubo, T. Goto, S. Inoue, H. Tanino, S. Sugiura, H. Kakoi, J. Am. Chem. Soc. 1972, 94, 9217
23. b) Y. Kishi, T. Fukuyama, M. Aratani, F. Nakatsubo, T. Goto, S. Inoue, H. Tanino, S. Sugiura, H. Kakoi, J. Am. Chem. Soc. 1972, 94, 9219.
24. a) T. Nishikawa, M. Asai, N. Ohyabu, N. Yamamoto, M. Isobe, Angew. Chem., Int. Ed. 1999, 38, 3081
25. b) M. Asai, T. Nishikawa, N. Ohyabu, N. Yamamoto, M. Isobe, Tetrahedron 2001, 57, 4543.
26. a) N. Ohyabu, T. Nishikawa, M. Isobe, J. Am. Chem. Soc. 2003, 125, 879
27. b) M. Isobe, N. Ohyabu, T. Nishikawa, J. Synth. Org. Chem., Jpn. 2007, 65, 492 (in Japanese).
28. A. Hinman, J. Du Bois, J. Am. Chem. Soc. 2003, 125, 11510.
29. a) T. Nishikawa, D. Urabe, M. Isobe, Angew. Chem., Int. Ed. 2004, 43, 4782
30. b) D. Urabe, T. Nishikawa, M. Isobe, Chem. Asian J. 2006, 1, 125.
31. a) K. Sato, S. Akai, H. Shoji, S. Yoshida, Y. Nagai, K. Suzuki, Y. Nakamura, Y. Kajihara, M. Funabashi, J. Yoshimura, J. Org. Chem. 2008, 73, 1234
32. b) K. Sato, S. Akai, N. Sugita, T. Ohsawa, T. Kogure, H. Shoji, J. Yoshimura, J. Org. Chem. 2005, 70, 7496.
33. For the total synthesis of 5,6,11-trideoxytetrodotoxin, a naturally occurring analogue, see:, T. Umezawa, T. Hayashi, H. Sakai, H. Teramoto, T. Yoshikawa, M. Izumida, Y. Tamatani, T. Hirose, Y. Ohfune, T. Shinada, Org. Lett. 2006, 8, 4971.
34. Tetrodotoxin, Saxitoxin, and the Molecular Biology of the Sodium Channel (Ann. N. Y. Acad. Sci. Vol. 479) (Eds.:, C. Y. Kao, S. R. Levinson,), New York, 1986.
35. M. Ueda, Chem. Lett. 2012, 41, 658.
36. a) T. Narahashi, J. W. Moore, W. Scott, J. Gen. Physiol. 1964, 47, 965
37. b) T. Narahashi, J. Toxicol., Toxin Rev. 2001, 20, 67
38. c) T. Narahashi, Proc. Jpn. Acad., Ser. B 2008, 84, 147.
39. S. Numa, M. Noda, in Tetrodotoxin, Saxitoxin, and the Molecular Biology of the Sodium Channel (Ann. N. Y. Acad. Sci. Vol. 479) (Eds.:, C. Y. Kao, S. R. Levinson,), New York, 1986, p. 338.
40. H. Terlau, S. H. Heinemann, W. Stühmer, M. Pusch, F. Conti, K. Imoto, S. Numa, FEBS Lett. 1991, 293, 93.
41. H. S. Mosher, F. A. Fuhrman, H. D. Buchwald, H. G. Fischer, Science 1964, 144, 1100.
42. K. Miyazawa, T. Noguchi, J. Toxicol., Toxin Rev. 2001, 20, 11.
43. U. Shimizu, H. Matsui, H. Sato, K. Yamamori, Mar. Sci. Mon. 1984, 16, 560 (in Japanese).
44. a) T. Yasumoto, D. Yasumura, M. Yotsu, T. Michishita, A. Endo, Y. Kotaki, Agric. Biol. Chem. 1986, 50, 793
45. b) T. Noguchi, J. K. Jeon, O. Arakawa, H. Sugita, Y. Deguchi, Y. Shida, K. Hashimoto, J. Biochem. 1986, 99, 311.
46. T. Noguchi, O. Arakawa, Mar. Drugs 2008, 6, 220.
47. Review:, R. Chau, J. A. Kalaitzis, B. A. Neilan, Aquat. Toxicol. 2011, 104, 61.
48. M. Yotsu-Yamashita, K. Nishimori, Y. Nitanai, M. Isemura, A. Sugimoto, T. Yasumoto, Biochem. Biophys. Res. Commun. 2000, 267, 403.
49. a) T. Matsui, K. Yamamori, K. Furukawa, M. Kono, Toxicon 2000, 38, 463
50. b) M. Yotsu-Yamashita, A. Sugimoto, T. Terakawa, Y. Shoji, T. Miyazawa, T. Yasumoto, Eur. J. Biochem. 2001, 268, 5937.
51. K. Matsumura, Nature 1995, 378, 563.
52. M. Isobe, N. Yamamoto, T. Nishikawa, in Levoglucosenone and Levoglucosans: Chemistry and Applications (Ed.:, Z. J. Witczak,), ATL Press, 1994, pp. 99-118.
53. For the initial synthetic efforts of a functionalized cyclohexene with a lactone of tetrodotoxin in our laboratory, see:, M. Isobe, T. Nishikawa, S. Pikul, T. Goto, Tetrahedron Lett. 1987, 28, 6485.
54. M. Isobe, T. Nishikawa, S. Pikul, unpublished.
55. M. Isobe, Y. Fukuda, T. Nishikawa, P. Chabert, T. Kawai, T. Goto, Tetrahedron Lett. 1990, 31, 3327.
56. a) M. Bamba, T. Nishikawa, M. Isobe, Tetrahedron Lett. 1996, 37, 8199
57. b) M. Bamba, T. Nishikawa, M. Isobe, Synlett 1998, 371
58. c) M. Bamba, T. Nishikawa, M. Isobe, Tetrahedron 1998, 54, 6639.
59. Y. Kishi, J. Synth. Org. Chem., Jpn. 1974, 32, 855 (in Japanese).
60. T. Nishikawa, M. Asai, N. Ohyabu, N. Yamamoto, Y. Fukuda, M. Isobe, Tetrahedron 2001, 57, 3875.
61. T. Nishikawa, M. Asai, N. Ohyabu, M. Isobe, J. Org. Chem. 1998, 63, 188.
62. T. Tsujimoto, T. Nishikawa, D. Urabe, M. Isobe, Synlett 2005, 433.
63. a) T. Nishikawa, D. Urabe, K. Yoshida, T. Iwabuchi, M. Asai, M. Isobe, Org. Lett. 2002, 4, 2679
64. b) T. Nishikawa, D. Urabe, K. Yoshida, T. Iwabuchi, M. Asai, M. Isobe, Chem. Eur. J. 2004, 10, 452.
65. T. Nishikawa, M. Asai, M. Isobe, J. Am. Chem. Soc. 2002, 124, 7847.
66. E. Weygand, E. Frauendorfer, Chem. Ber. 1970, 103, 2437.
67. T. Oishi, K. Ando, K. Inomiya, H. Sato, M. Iida, N. Chida, Org. Lett. 2002, 4, 151.
68. K. Tsuda, M. Kawamura, Pharm. Bull. Jpn. 1953, 1, 112.
69. a) N. Yamamoto, M. Isobe, Chem. Lett. 1994, 23, 2299
70. b) T. Nishikawa, N. Ohyabu, N. Yamamoto, M. Isobe, Tetrahedron 1999, 57, 4325.
71. M. Yotsu-Yamashita, D. Urabe, M. Asai, T. Nishikawa, M. Isobe, Toxicon 2003, 42, 557.
72. C. Rosker, B. Lohberger, D. Hofer, B. Steinecker, S. Quasthoff, W. Schreibmayer, Am. J. Physiol.: Cell. Physiol. 2007, 293, C783.
73. F. R. Nieto, E. J. Cobos, M. Á. Tejada, C. Sánchez- Fernández, R. González-Cano, C. M. Cendán, Mar. Drugs 2012, 10, 281.
74. Y. Satake, T. Nishikawa, T. Hiramatsu, H. Araki, M. Isobe, Synthesis 2010, 1992.