Stereocontrolled synthesis of (-)-5,11-dideoxytetrodotoxin

Angewandte Chemie - International Edition

Volumn 38, Issue 20, 1999, Pages 3081-3084

  Nishikawa, Toshio ^a   Asai, Masanori ^a   Ohyabu, Norio ^a   Yamamoto, Noboru ^a   Isobe, Minoru ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Asymmetric synthesis; Natural products; Synthetic methods; Tetrodotoxins

Indexed keywords

5,11 DIDEOXYTETRODOXIN; TETRODOTOXIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ENANTIOMER; MOLECULAR STABILITY; STEREOCHEMISTRY; TOXIN SYNTHESIS;

EID: 0033581622     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991018)38:20<3081::AID-ANIE3081>3.0.CO;2-6     Document Type: Article

References (46)

1. For the structure: a) T. Goto, Y. Kishi, S. Takahashi, Y. Hirata, Tetrahedron 1965, 21, 2059-2088;
2. b) K. Tsuda, S. Ikuma, M. Kawamura, K. Tachikawa, K. Sakai, C. Tamura, O. Akamatsu, Chem. Pharm. Bull. 1964, 12, 1357-1374;
3. R. B. Woodward, Pure Appl. Chem. 1964, 9, 49-74.
4. T. Narahashi, Physiol. Rev. 1974, 54, 813-889.
5. a) 5,6,11-Trideoxytetrodoloxin: M. Yotsu-Yamashita, Y. Yamagishi, T. Yasumoto, Tetrahedron Lett. 1995, 51, 9329-9332;
6. b) 1-hydroxy-5,11-dideoxytetrodotoxin: Y. Kotaki, Y. Shimizu, J. Am. Chem. Soc. 1993, 115, 827-830;
7. c) 6-epi- and 11-deoxytetrodotoxin: T. Yasumoto, M. Yotsu, M. Murata, H. Naoki, J. Am. Chem. Soc. 1988, 110, 2344-2345.
8. "Tetrodotoxin, Saxitoxin, and the Molecular Biology of the Sodium Channel": Ann. N.Y. Acad. Sci. 1986, 479 (review series).
9. a) H. Nakayama, Y. Hatanaka, M. Takai, E. Yoshida, Y. Kanaoka, Ann. N.Y. Acad. Sci. 1993, 707, 349;
10. b) G. M. Lipkind, H. A. Fozzard, Biophys. J. 1994, 66, 1-33.
11. Tetrodotoxin was identified as a pheromonelike substance among the puffer fish. K. Matsumura, Nature 1995, 378, 563.
12. For examples of some labeled tetrodotoxin derivatives, see: a) M. Balerna, A. Lombet, R. Chicheportiche, G. Romey, M. Lazdunski, Biochim. Biophys. Acta 1981, 644, 219-225;
13. b) J. Bontemps, R. Cantineau, C. Grandfils, P. Leprince, G. Dandrifosse, E. Schoffeniels, Anal. Biochem. 1984, 139, 149- 157;
14. B. Q. Wu, L. Yang, C. Y. Kao, S. R. Levinson, M. Yotsu-Yamashita, T. Yasumoto, Toxicon 1996, 34, 407-416.
15. Recent reports: a) B. Noya, R. Alonso, Tetrahedron Lett. 1997, 38, 2745-2748;
16. b) C.S. Burgey, R. Vollerthun, B. Fraser-Reid, J. Org. Chem. 1996, 61, 1609-1618;
17. c) K. Sato, Y. Kajihara, Y. Nakamura, J. Yoshimura, Chem. Lett. 1991, 1559-1562;
18. d) J. F. W. Keana, J. S. Bland, P. J. Boyle, M. Erion, R. Hartling, J. R. Husman, R. B. Roman, G. Ferguson, M. Parvez, J. Org. Chem. 1983, 48, 3627-3631; J. F. W. Keana, P. J. Boyle, M. Erion, R. Hartling, J. R. Husman, J. E. Richman, R. M. Wah, J. Org. Chem. 1983, 48, 3621-3626.
19. d) J. F. W. Keana, J. S. Bland, P. J. Boyle, M. Erion, R. Hartling, J. R. Husman, R. B. Roman, G. Ferguson, M. Parvez, J. Org. Chem. 1983, 48, 3627-3631; J. F. W. Keana, P. J. Boyle, M. Erion, R. Hartling, J. R. Husman, J. E. Richman, R. M. Wah, J. Org. Chem. 1983, 48, 3621-3626.
20. 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, 9217-9219;
21. 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, 9219-9221;
22. c) Y Kishi, F. Nakatsubo, M. Aratani, T. Goto, S. Inoue, H. Kakoi, S. Sugiura, Tetrahedron Lett. 1970, 5127-5128;
23. d) Y. Kishi, F. Nakatsubo, M. Aratani, T. Goto, S. Inoue, H. Kakoi, Tetrahedron Lett. 1970, 5129-5132.
24. M. Isobe, T. Nishikawa, S. Pikul, T. Goto, Tetrahedron Lett. 1987, 28, 6485-6488.
25. Reviews: a) L. E. Overman, Acc. Chem. Res. 1980, 13, 218-224;
26. b) K. Ritter in Stereoselective Synthesis (Houben-Weyl) Vol. 21/9 E21, Vol. 9 (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1996, pp. 5677-5699.
27. M. Isobe, F. Fukuda, T. Nishikawa, P. Chabert, T. Kawai, T. Goto, Tetrahedron Lett. 1990, 31, 3327-3330.
28. a) N. Yamamoto, M. Isobe, Chem. Lett. 1994, 2299-2302;
29. b) T. Nishikawa, N. Ohyabu, N. Yamamoto, M. Isobe, Tetrahedron 1999, 55, 4325-4340.
30. M. Isobe, N. Yamamoto, T. Nishikawa in Levoglucosenone and Levoglucosans, Chemistry and Applications (Ed.: Z. J. Witczak), ATL Press, 1994, pp. 99-118.
31. T. Nishikawa, M. Asai, N. Ohyabu, M. Isobe, J. Org. Chem. 1998, 63, 188-192.
32. H. W. Pauls, B. Fraser-Reid, Carbotrydr. Res. 1986, 150, 111-119.
33. 2) reported by Danishefsky et al. gave our desired product 4 in better yield and with higher selectivity; S. J. Danishefsky, H. G. Selnick, R. E. Zelle, M. P. DeNinno, J. Am. Chem. Soc. 1988, 110, 4368-4378.
34. 2) reported by Danishefsky et al. gave our desired product 4 in better yield and with higher selectivity; S. J. Danishefsky, H. G. Selnick, R. E. Zelle, M. P. DeNinno, J. Am. Chem. Soc. 1988, 110, 4368-4378.
35. The stereochemistry was controlled by a steric factor rather than an orientation of the neighboring hydroxy group; see ref. [9d].
36. N. Yamamoto, T. Nishikawa, M. Isobe, Synlett 1995, 505-506.
37. P. H. Carisen, T. Katsuki, V. S. Martin, K. B. Sharpless. J. Org. Chem. 1981, 46, 3936-3938.
38. Determination of the configuration at the C9 position is included in the Supporting Information.
39. J. Petrov, I. Atanassova, A. Balabanova, N. Mollov, Izv. Khim. 1990, 23, 53-57.
40. Detailed analysis of the crude product revealed that one of the products lacked H9, indicating that an oxidation occurred at the C9 position. Kishi et al. reported on the lability of the acetoxy group at the C9 position in their total synthesis of tetrodotoxin. See: a) ref. [9b];
41. b) H. Tanino, S. Inoue, M. Aratani, Y, Kishi, Tetrahedron Lett. 1974, 335-338.
42. M. Xie, D. A. Berges, M. J. Robins, J. Org. Chem. 1996, 61, 5178-5179.
43. K. Mori, M. Tominaga, T. Takigawa, M. Matsui, Synthesis 1973, 790-791.
44. [13b]
45. [13b]
46. [3a] Compound 22 is the first example of 4,9-anhydrotetrodotoxin among a series of 5-deoxytetrodotoxin analogues.