New synthetic route of guanidine from trichloroacetamide for tetrodotoxin and its related compounds

Tetrahedron

Volumn 55, Issue 14, 1999, Pages 4325-4340

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

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Guanidine; Hydrogenolysis; Protecting group; Toxins

Indexed keywords

ACETAMIDE DERIVATIVE; GUANIDINE; TETRODOTOXIN;

ARTICLE; CHEMICAL REACTION; DEALKYLATION; HIGH TEMPERATURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRESSURE; PRIORITY JOURNAL; SYNTHESIS;

EID: 0033119493     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00140-4     Document Type: Article

References (54)

1. For recent reviews, see: Berlinck, R. G. S. Prog. Chem. Org. Nat. Prod. 1995, 66, 120-295.
2. (b) Berlinck, R. G. S. Nat. Prod. Rep. 1996, 377-409.
3. For a review: Yamamoto, Y.; Kojima, S. In The Chemistry of Amidines and Imidates; Patai. S.; Rappoport, Z., Eds.; John Wiley & Sons: New York, 1991; Vol. 2; Chapter 10, p 486-526.
4. For a review: Schow, S. In Encyclopedia of Reagents for Organic Synthesis, Paquette, L.A. Ed. Wiley: Sussex UK, 1996, p 1408-1410.
5. Reviews on carbodiimide: (a) Williams, A.; Ibrahim, I. T. Chem. Rev. 1981, 81, 589-636.
6. (b) Mikolajczyk, M.; Kielbasinski, O. Tetrahedron 1981, 37, 233-284.
7. Recent leading references: (a) Poss, M. A.; Iwanowicz, E.; Reid, J. A.; Lin, J.; Gu, Z. Tetrahedron Lett. 1992, 33, 5933-5936.
8. (b) Kim, K. S.; Qian, L. Tetrahedron Lett. 1993, 34, 7677-7680.
9. (c) Levallet, C.; Lerpiniere, J.; Ko, S. Y. Tetrahedron 1997, 53, 5291-5304.
10. (d) Yong, Y. F.; Kowalski, J. A.; Lipton, M. A. J. Org. Chem. 1997, 62, 1540-1542.
11. Recent leading references: (a) Bergeron, R. J.; McManis, J. S. J. Org. Chem. 1987, 52, 1700-1703.
12. (b) Tian, Z.; Edwards, P.; Roeske, R. W. Int. J. Peptide Protein Res. 1992, 40, 119-126.
13. (c) Chandrakumar, N. S. Synth. Commun. 1996, 26, 2613-2616.
14. (d) Palmer, D. C. In Encyclopedia of Reagents for Organic Synthesis, Paquette, L.A. Ed. Wiley: Sussex UK, 1996, p 3523-3525.
15. (a) Miller, A. In Encyclopedia of Reagents for Organic Synthesis, Paquette, L.A. Ed. Wiley: Sussex UK, 1996, p 176-178.
16. (b) Miller, A. E.; Bischoff, J. J. Synthesis 1986, 777-779.
17. (c) Kim, K.; Lin, Y.- T.; Mosher, H. S. Tetrahedron Lett. 1988, 29, 3183-3186.
18. (a) Bernatowicz, M. S. In Encyclopedia of Reagents for Organic Synthesis, Paquette, L.A. Ed. Wiley: Sussex UK, 1996, p 4343-4344.
19. (b) Bernatowicz, M. S.; Wu, Y.; Matsueda, G. R. Tetrahedron Lett. 1993, 34, 3389-3392.
20. (c) Drake, B.; Patek, M.; Leble, M. Synthesis 1994, 579- 582.
21. Quite recently, bisprotected guanidine triflate was reported as efficient guanidinylation reagent.: Feichtinger, K.; Zapf, C.; Sings, H. L.; Goodman, M. J. Org. Chem. 1998, 63, 3804-3805.
22. (a) Isobe, M.; Fukuda, Y.; Nishikawa, T.; Chabert, P.; Kawai, T.; Goto, T. Tetrahedron Lett. 1990, 31, 3327-3330.
23. (b) Yamamoto, N.; Nishikawa, T.; Isobe, M. Synlett 1995, 505-506.
24. (c) Bamba, M.; Nishikawa, T.; Isobe, M. Tetrahedron 1998, 54, 6639-6650.
25. For the structure: (a) Goto, T.; Kishi, Y.; Takahashi, S.; Hirata, Y. Tetrahedron 1965, 21, 2059-2088.
26. (b) Tsuda, K.; Ikuma, S.; Kawamura, M.; Tachikawa, R.; Sakai, K.; Tamura, C.; Amakasu, O. Chem. Pharm. Bull. 1964, 12, 1357-1374.
27. (c) Woodward, R. B. Pure. Appl. Chem. 1964, 9, 49-74.
28. For racemic total synthesis: (a) Kishi, Y.; Aratani, M.; Fukuyama, T.; Nakatsubo, F.; Goto, T.; Inoue, S.; Tanino, H.; Sugiura, S.; Kakoi, H. J. Am. Chem. Soc. 1972, 94, 9217-9219.
29. (b) Kishi, Y.; Fukuyama, T.; Aratani, M.; Nakatsubo, F.; Goto, T.; Inoue, S.; Tanino, H.; Sugiura, S.; Kakoi, H. J. Am. Chem. Soc. 1972, 94, 9219-9221.
30. For recent reports on the synthetic efforts from other laboratories: (a) Burgey, C. S.; Vollerthun, R.; Fraser-Reid, B. J. Org. Chem. 1996, 67, 1609-1618.
31. (b) Sato, K.; Kajihara, Y.; Nakamura, Y.; Yoshimura, J. Chem. Lett. 1991, 1559-1562.
32. (c) Keana, J. F. W.; Bland, J. S.; Boyle, P. J.; Erion, M.; Hartling, R.; Husman, J. R.; Roman, R. B. J. Org. Chem. 1983, 48, 3627-3631.
33. 10a on the synthesis of a simple model compound of tetrodotoxin, we used harsh conditions (6N NaOH/EtOH, 50 °C, 12 h) to deprotect the trichloroacetamide.
34. Yamamoto, N.; Isobe, M. Chem. Lett. 1994, 2299-2302.
35. Review on the Overman rearrangement: (a) Overman, L. E. Acc. Chem. Res. 1980, 13, 218-224.
36. (b) Ritter, K. In Houben-Weyl. Stereoselective Synthesis. E 21, Vol. 9; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1996; p 5677-5699.
37. Petrov, J.; Atanassova, I.; Balabanova, A.; Mollov, N. Izv. Khim. 1990, 23, 53-57.
38. Clizbe, L. A.; Overman, L. E. Org. Synth. 1988, Coll. Vol. 6, 507-511.
39. Treatment of 6 with benzylamine hydrochloride in DMF at 100 °C for 3.5 h gave a mixture of the dibenzylguanidinium chloride 7 (23% from 5) and the urea 5.
40. (a) Greene, T. W.; Wuts, P. G. Protective Groups in Organic Synthesis, 2nd Ed., John Wiley & Sons, Inc. 1991, p 364-366.
41. (b) Kocienski, P. J. Protecting Groups, Georg Thieme Verlag, 1994, p 220- 227.
42. We have not examined Birch reduction conditions for debenzylation, because we considered that such conditions would not be compatible with a variety of functional groups of tetrodotoxin molecule.
43. Johnstone, R. A. W.; Wilby, A. H. Chem. Rev. 1985, 85, 129-170.
44. For other example: Hong, C. Y.; Kishi, Y. J. Am. Chem. Soc. 1991, 113, 9693-9694.
45. 4, see: (a) Carisen, P. H.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938. formula presented
46. 4, see: (a) Carisen, P. H.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938. formula presented
47. Isobe, M.; Yamamoto, N.; Nishikawa, T. In Levoglucosenone and Levoglucosans, Chemistry and Applications. Witczak, Z. J. Ed.; ATL PRESS, pp. 99-118, 1994.
48. Nishikawa, T.; Asai, M.; Ohyabu, N.; Isobe, M. J. Org. Chem. 1998, 63, 188-192.
49. The by-product was tetraol iii as a single stereoisomer (18%) whose stereochemistry (*) was not determined. formula presented
50. 2) also yielded the product, but the reactions were very slow.
51. Yasumoto, T.; Yotsu, M.; Murata, M.; Naoki, H. J. Am. Chem. Soc. 1988, 110, 2344-2345.
52. The structure was iv, which was hydrogenated to give guanidinium compound v having no aminal moiety found in tetrodotoxin. formula presented
53. 1H NMR spectrum. These ratios were comparable to those of the debenzylated products 3a and 3b.
54. General experimental details have been described: réf. 26.