Stereoselective synthesis of the fully functionalized HIJ-ring framework of ciguatoxin

Synlett

Volumn , Issue 4, 2004, Pages 603-608

  Baba, Takayuki ^a   Takai, Shigeyuki ^a   Sawada, Naotaka ^a   Isobe, Minoru ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Alkyne cobalt complexes; Ciguatoxin; Intramolecular 1,4 addition reaction; Medium sized ring closure reaction; Reductive decomplexation

Indexed keywords

ACETYLENE; CIGUATOXIN; COBALT;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; FISH; FOOD POISONING; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 1642293104     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-817769     Document Type: Article

References (42)

1. For reviews, see: (a) Gillespie, N. C.; Lewis, R. J.; Pearn, J.; Bourke, A. T. C.; Helms, M. J.; Bourke, J. B.; Shields, W. J. Ned. J. Aust. 1986, 145, 584. (b) Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897. (c) Scheuer, P. J. Tetrahedron 1994, 50, 3. (d) Yasumoto, T. Chem. Rec. 2001, 1, 228. (e) Lewis, R. J. Toxicon 2001, 39, 97.
2. For reviews, see: (a) Gillespie, N. C.; Lewis, R. J.; Pearn, J.; Bourke, A. T. C.; Helms, M. J.; Bourke, J. B.; Shields, W. J. Ned. J. Aust. 1986, 145, 584. (b) Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897. (c) Scheuer, P. J. Tetrahedron 1994, 50, 3. (d) Yasumoto, T. Chem. Rec. 2001, 1, 228. (e) Lewis, R. J. Toxicon 2001, 39, 97.
3. For reviews, see: (a) Gillespie, N. C.; Lewis, R. J.; Pearn, J.; Bourke, A. T. C.; Helms, M. J.; Bourke, J. B.; Shields, W. J. Ned. J. Aust. 1986, 145, 584. (b) Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897. (c) Scheuer, P. J. Tetrahedron 1994, 50, 3. (d) Yasumoto, T. Chem. Rec. 2001, 1, 228. (e) Lewis, R. J. Toxicon 2001, 39, 97.
4. For reviews, see: (a) Gillespie, N. C.; Lewis, R. J.; Pearn, J.; Bourke, A. T. C.; Helms, M. J.; Bourke, J. B.; Shields, W. J. Ned. J. Aust. 1986, 145, 584. (b) Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897. (c) Scheuer, P. J. Tetrahedron 1994, 50, 3. (d) Yasumoto, T. Chem. Rec. 2001, 1, 228. (e) Lewis, R. J. Toxicon 2001, 39, 97.
5. For reviews, see: (a) Gillespie, N. C.; Lewis, R. J.; Pearn, J.; Bourke, A. T. C.; Helms, M. J.; Bourke, J. B.; Shields, W. J. Ned. J. Aust. 1986, 145, 584. (b) Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897. (c) Scheuer, P. J. Tetrahedron 1994, 50, 3. (d) Yasumoto, T. Chem. Rec. 2001, 1, 228. (e) Lewis, R. J. Toxicon 2001, 39, 97.
6. For the origin of CTXs, see: Yasumoto, T.; Nakajima, R.; Bagnis, R.; Adachi, R. Nippon Suisan Gakkaishi 1977, 43, 1021.
7. For the characterization of CTXs, see: (a) Scheuer, P. J.; Takahashi, W. ; Tsutsumi, J.; Yoshida, T. Science 1967, 155, 1267. (b) Tachibana, K. Ph.D. Thesis; University of Hawaii: Hawaii, 1980. (c) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Yasumoto, T. J. Am. Chem. Soc. 1989, 111, 8929. (d) Murata, M.; Legrand, A. M.; Yasumoto, T. Tetrahedron Lett. 1989, 30, 3793. (e) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380. (f) Murata, M.; Legrand, A. M.; Scheuer, P. J.; Yasumoto, T. Tetrahedron Lett. 1992, 33, 525. (g) Satake, M.; Morohashi, A.; Oguri, H.; Oishi, T.; Hirama, M.; Harada, N.; Yasumoto, T. J. Am. Chem. Soc. 1997, 119, 11325.
8. For the characterization of CTXs, see: (a) Scheuer, P. J.; Takahashi, W. ; Tsutsumi, J.; Yoshida, T. Science 1967, 155, 1267. (b) Tachibana, K. Ph.D. Thesis; University of Hawaii: Hawaii, 1980. (c) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Yasumoto, T. J. Am. Chem. Soc. 1989, 111, 8929. (d) Murata, M.; Legrand, A. M.; Yasumoto, T. Tetrahedron Lett. 1989, 30, 3793. (e) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380. (f) Murata, M.; Legrand, A. M.; Scheuer, P. J.; Yasumoto, T. Tetrahedron Lett. 1992, 33, 525. (g) Satake, M.; Morohashi, A.; Oguri, H.; Oishi, T.; Hirama, M.; Harada, N.; Yasumoto, T. J. Am. Chem. Soc. 1997, 119, 11325.
9. For the characterization of CTXs, see: (a) Scheuer, P. J.; Takahashi, W. ; Tsutsumi, J.; Yoshida, T. Science 1967, 155, 1267. (b) Tachibana, K. Ph.D. Thesis; University of Hawaii: Hawaii, 1980. (c) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Yasumoto, T. J. Am. Chem. Soc. 1989, 111, 8929. (d) Murata, M.; Legrand, A. M.; Yasumoto, T. Tetrahedron Lett. 1989, 30, 3793. (e) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380. (f) Murata, M.; Legrand, A. M.; Scheuer, P. J.; Yasumoto, T. Tetrahedron Lett. 1992, 33, 525. (g) Satake, M.; Morohashi, A.; Oguri, H.; Oishi, T.; Hirama, M.; Harada, N.; Yasumoto, T. J. Am. Chem. Soc. 1997, 119, 11325.
10. For the characterization of CTXs, see: (a) Scheuer, P. J.; Takahashi, W. ; Tsutsumi, J.; Yoshida, T. Science 1967, 155, 1267. (b) Tachibana, K. Ph.D. Thesis; University of Hawaii: Hawaii, 1980. (c) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Yasumoto, T. J. Am. Chem. Soc. 1989, 111, 8929. (d) Murata, M.; Legrand, A. M.; Yasumoto, T. Tetrahedron Lett. 1989, 30, 3793. (e) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380. (f) Murata, M.; Legrand, A. M.; Scheuer, P. J.; Yasumoto, T. Tetrahedron Lett. 1992, 33, 525. (g) Satake, M.; Morohashi, A.; Oguri, H.; Oishi, T.; Hirama, M.; Harada, N.; Yasumoto, T. J. Am. Chem. Soc. 1997, 119, 11325.
11. For the characterization of CTXs, see: (a) Scheuer, P. J.; Takahashi, W. ; Tsutsumi, J.; Yoshida, T. Science 1967, 155, 1267. (b) Tachibana, K. Ph.D. Thesis; University of Hawaii: Hawaii, 1980. (c) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Yasumoto, T. J. Am. Chem. Soc. 1989, 111, 8929. (d) Murata, M.; Legrand, A. M.; Yasumoto, T. Tetrahedron Lett. 1989, 30, 3793. (e) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380. (f) Murata, M.; Legrand, A. M.; Scheuer, P. J.; Yasumoto, T. Tetrahedron Lett. 1992, 33, 525. (g) Satake, M.; Morohashi, A.; Oguri, H.; Oishi, T.; Hirama, M.; Harada, N.; Yasumoto, T. J. Am. Chem. Soc. 1997, 119, 11325.
12. For the characterization of CTXs, see: (a) Scheuer, P. J.; Takahashi, W. ; Tsutsumi, J.; Yoshida, T. Science 1967, 155, 1267. (b) Tachibana, K. Ph.D. Thesis; University of Hawaii: Hawaii, 1980. (c) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Yasumoto, T. J. Am. Chem. Soc. 1989, 111, 8929. (d) Murata, M.; Legrand, A. M.; Yasumoto, T. Tetrahedron Lett. 1989, 30, 3793. (e) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380. (f) Murata, M.; Legrand, A. M.; Scheuer, P. J.; Yasumoto, T. Tetrahedron Lett. 1992, 33, 525. (g) Satake, M.; Morohashi, A.; Oguri, H.; Oishi, T.; Hirama, M.; Harada, N.; Yasumoto, T. J. Am. Chem. Soc. 1997, 119, 11325.
13. For the characterization of CTXs, see: (a) Scheuer, P. J.; Takahashi, W. ; Tsutsumi, J.; Yoshida, T. Science 1967, 155, 1267. (b) Tachibana, K. Ph.D. Thesis; University of Hawaii: Hawaii, 1980. (c) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Yasumoto, T. J. Am. Chem. Soc. 1989, 111, 8929. (d) Murata, M.; Legrand, A. M.; Yasumoto, T. Tetrahedron Lett. 1989, 30, 3793. (e) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380. (f) Murata, M.; Legrand, A. M.; Scheuer, P. J.; Yasumoto, T. Tetrahedron Lett. 1992, 33, 525. (g) Satake, M.; Morohashi, A.; Oguri, H.; Oishi, T.; Hirama, M.; Harada, N.; Yasumoto, T. J. Am. Chem. Soc. 1997, 119, 11325.
14. For the bioactivity of CTXs, see: (a) Lombert, A.; Bidard, J.-N.; Lazdunski, M. FEBS Lett. 1987, 219, 355. (b) Lewis, R. J.; Sellin, M.; Poli, M. A.; Norton, R. S.; Macleod, J. K.; Sheil, M. M. Toxicon 1991, 29, 1115. (c) Dechraoui, M.-Y.; Naar, J.; Pauillac, S.; Legrand, A.-M. Toxicon 1999, 37, 125. (d) Anger, T.; Madge, D.-J.; Mulla, M.; Riddall, D. J. Med. Chem. 2001, 44, 115. (e) Lin, Y.-Y.; Risk, M.; Ray, S. M.; Engen, D. V.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773. (f) Shimizu, Y.; Chou, H.-N.; Bando, H.; Duyne, G. V.; Clardy, J. C. J. Am. Chem. Soc. 1986, 108, 514.
15. For the bioactivity of CTXs, see: (a) Lombert, A.; Bidard, J.-N.; Lazdunski, M. FEBS Lett. 1987, 219, 355. (b) Lewis, R. J.; Sellin, M.; Poli, M. A.; Norton, R. S.; Macleod, J. K.; Sheil, M. M. Toxicon 1991, 29, 1115. (c) Dechraoui, M.-Y.; Naar, J.; Pauillac, S.; Legrand, A.-M. Toxicon 1999, 37, 125. (d) Anger, T.; Madge, D.-J.; Mulla, M.; Riddall, D. J. Med. Chem. 2001, 44, 115. (e) Lin, Y.-Y.; Risk, M.; Ray, S. M.; Engen, D. V.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773. (f) Shimizu, Y.; Chou, H.-N.; Bando, H.; Duyne, G. V.; Clardy, J. C. J. Am. Chem. Soc. 1986, 108, 514.
16. For the bioactivity of CTXs, see: (a) Lombert, A.; Bidard, J.-N.; Lazdunski, M. FEBS Lett. 1987, 219, 355. (b) Lewis, R. J.; Sellin, M.; Poli, M. A.; Norton, R. S.; Macleod, J. K.; Sheil, M. M. Toxicon 1991, 29, 1115. (c) Dechraoui, M.-Y.; Naar, J.; Pauillac, S.; Legrand, A.-M. Toxicon 1999, 37, 125. (d) Anger, T.; Madge, D.-J.; Mulla, M.; Riddall, D. J. Med. Chem. 2001, 44, 115. (e) Lin, Y.-Y.; Risk, M.; Ray, S. M.; Engen, D. V.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773. (f) Shimizu, Y.; Chou, H.-N.; Bando, H.; Duyne, G. V.; Clardy, J. C. J. Am. Chem. Soc. 1986, 108, 514.
17. For the bioactivity of CTXs, see: (a) Lombert, A.; Bidard, J.-N.; Lazdunski, M. FEBS Lett. 1987, 219, 355. (b) Lewis, R. J.; Sellin, M.; Poli, M. A.; Norton, R. S.; Macleod, J. K.; Sheil, M. M. Toxicon 1991, 29, 1115. (c) Dechraoui, M.-Y.; Naar, J.; Pauillac, S.; Legrand, A.-M. Toxicon 1999, 37, 125. (d) Anger, T.; Madge, D.-J.; Mulla, M.; Riddall, D. J. Med. Chem. 2001, 44, 115. (e) Lin, Y.-Y.; Risk, M.; Ray, S. M.; Engen, D. V.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773. (f) Shimizu, Y.; Chou, H.-N.; Bando, H.; Duyne, G. V.; Clardy, J. C. J. Am. Chem. Soc. 1986, 108, 514.
18. For the bioactivity of CTXs, see: (a) Lombert, A.; Bidard, J.-N.; Lazdunski, M. FEBS Lett. 1987, 219, 355. (b) Lewis, R. J.; Sellin, M.; Poli, M. A.; Norton, R. S.; Macleod, J. K.; Sheil, M. M. Toxicon 1991, 29, 1115. (c) Dechraoui, M.-Y.; Naar, J.; Pauillac, S.; Legrand, A.-M. Toxicon 1999, 37, 125. (d) Anger, T.; Madge, D.-J.; Mulla, M.; Riddall, D. J. Med. Chem. 2001, 44, 115. (e) Lin, Y.-Y.; Risk, M.; Ray, S. M.; Engen, D. V.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773. (f) Shimizu, Y.; Chou, H.-N.; Bando, H.; Duyne, G. V.; Clardy, J. C. J. Am. Chem. Soc. 1986, 108, 514.
19. For the bioactivity of CTXs, see: (a) Lombert, A.; Bidard, J.-N.; Lazdunski, M. FEBS Lett. 1987, 219, 355. (b) Lewis, R. J.; Sellin, M.; Poli, M. A.; Norton, R. S.; Macleod, J. K.; Sheil, M. M. Toxicon 1991, 29, 1115. (c) Dechraoui, M.-Y.; Naar, J.; Pauillac, S.; Legrand, A.-M. Toxicon 1999, 37, 125. (d) Anger, T.; Madge, D.-J.; Mulla, M.; Riddall, D. J. Med. Chem. 2001, 44, 115. (e) Lin, Y.-Y.; Risk, M.; Ray, S. M.; Engen, D. V.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773. (f) Shimizu, Y.; Chou, H.-N.; Bando, H.; Duyne, G. V.; Clardy, J. C. J. Am. Chem. Soc. 1986, 108, 514.
20. (a) Hirama, M.; Oishi, T.; Uehara, H.; Inoue, M.; Maruyama, M.; Oguri, H.; Satake, M. Science 2001, 294, 1904.
21. (b) Inoue, M.; Uehara, H.; Maruyama, M.; Hirama, M. Org. Lett. 2002, 4, 4551.
22. (c) Tatami, A.; Inoue, M.; Uehara, H.; Hirama, M. Tetrahedron Lett. 2003, 44, 5229.
23. For recent synthetic studies of ciguatoxin in our laboratory, see: (a) Saeeng, R.; Isobe, M. Heterocycles 2001, 54, 789. (b) Kira, K.; Hamajima, A.; Isobe, M. Tetrahedron 2002, 58, 1875. (c) Takai, S.; Sawada, N.; Isobe, M. J. Org. Chem. 2003, 68, 3225. (d) Baba, T.; Huang, G.; Isobe, M. Tetrahedron 2003, 59, 6851; and references therein.
24. For recent synthetic studies of ciguatoxin in our laboratory, see: (a) Saeeng, R.; Isobe, M. Heterocycles 2001, 54, 789. (b) Kira, K.; Hamajima, A.; Isobe, M. Tetrahedron 2002, 58, 1875. (c) Takai, S.; Sawada, N.; Isobe, M. J. Org. Chem. 2003, 68, 3225. (d) Baba, T.; Huang, G.; Isobe, M. Tetrahedron 2003, 59, 6851; and references therein.
25. For recent synthetic studies of ciguatoxin in our laboratory, see: (a) Saeeng, R.; Isobe, M. Heterocycles 2001, 54, 789. (b) Kira, K.; Hamajima, A.; Isobe, M. Tetrahedron 2002, 58, 1875. (c) Takai, S.; Sawada, N.; Isobe, M. J. Org. Chem. 2003, 68, 3225. (d) Baba, T.; Huang, G.; Isobe, M. Tetrahedron 2003, 59, 6851; and references therein.
26. For recent synthetic studies of ciguatoxin in our laboratory, see: (a) Saeeng, R.; Isobe, M. Heterocycles 2001, 54, 789. (b) Kira, K.; Hamajima, A.; Isobe, M. Tetrahedron 2002, 58, 1875. (c) Takai, S.; Sawada, N.; Isobe, M. J. Org. Chem. 2003, 68, 3225. (d) Baba, T.; Huang, G.; Isobe, M. Tetrahedron 2003, 59, 6851; and references therein.
27. For a review of the Nicholas reaction, see: Teobald, B. J. Tetrahedron 2002, 58, 4133.
28. For construction of medium sized ether rings via acetylene cobalt complexes in a highly stereoselective syn-trans orientation, see: (a) Isobe, M. ; Yenjai, C.; Tanaka, S. Synlett 1994, 11, 916. (b) Yenjai, C.; Isobe, M. Tetrahedron 1998, 54, 2509. (c) Isobe, M.; Hosokawa, S.; Kira, K. Chem. Lett. 1996, 473. (d) Isobe, M.; Nishizawa, R.; Hosokawa, S.; Nishikawa, T. Chem. Commun. 1998, 2665.
29. For construction of medium sized ether rings via acetylene cobalt complexes in a highly stereoselective syn-trans orientation, see: (a) Isobe, M. ; Yenjai, C.; Tanaka, S. Synlett 1994, 11, 916. (b) Yenjai, C.; Isobe, M. Tetrahedron 1998, 54, 2509. (c) Isobe, M.; Hosokawa, S.; Kira, K. Chem. Lett. 1996, 473. (d) Isobe, M.; Nishizawa, R.; Hosokawa, S.; Nishikawa, T. Chem. Commun. 1998, 2665.
30. For construction of medium sized ether rings via acetylene cobalt complexes in a highly stereoselective syn-trans orientation, see: (a) Isobe, M. ; Yenjai, C.; Tanaka, S. Synlett 1994, 11, 916. (b) Yenjai, C.; Isobe, M. Tetrahedron 1998, 54, 2509. (c) Isobe, M.; Hosokawa, S.; Kira, K. Chem. Lett. 1996, 473. (d) Isobe, M.; Nishizawa, R.; Hosokawa, S.; Nishikawa, T. Chem. Commun. 1998, 2665.
31. For construction of medium sized ether rings via acetylene cobalt complexes in a highly stereoselective syn-trans orientation, see: (a) Isobe, M. ; Yenjai, C.; Tanaka, S. Synlett 1994, 11, 916. (b) Yenjai, C.; Isobe, M. Tetrahedron 1998, 54, 2509. (c) Isobe, M.; Hosokawa, S.; Kira, K. Chem. Lett. 1996, 473. (d) Isobe, M.; Nishizawa, R.; Hosokawa, S.; Nishikawa, T. Chem. Commun. 1998, 2665.
32. Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976.
33. Smidt, J.; Hafner, W.; Jira, R.; Sieber, R.; Sedlmeier, J.; Sabel, A. Angew. Chem., Int. Ed. Engl. 1962, 1, 80.
34. For reductive decomplexation reaction into cis-olefins or vinylsilanes, see: (a) Hosokawa, S.; Isobe, M. Tetrahedron Lett. 1998, 39, 2609. (b) Shibuya, S.; Isobe, M. Tetrahedron 1998, 54, 6677. (c) Takai, S.; Ploypradith, P.; Hamajima, A.; Kira, K.; Isobe, M. Synlett 2002, 588.
35. For reductive decomplexation reaction into cis-olefins or vinylsilanes, see: (a) Hosokawa, S.; Isobe, M. Tetrahedron Lett. 1998, 39, 2609. (b) Shibuya, S.; Isobe, M. Tetrahedron 1998, 54, 6677. (c) Takai, S.; Ploypradith, P.; Hamajima, A.; Kira, K.; Isobe, M. Synlett 2002, 588.
36. For reductive decomplexation reaction into cis-olefins or vinylsilanes, see: (a) Hosokawa, S.; Isobe, M. Tetrahedron Lett. 1998, 39, 2609. (b) Shibuya, S.; Isobe, M. Tetrahedron 1998, 54, 6677. (c) Takai, S.; Ploypradith, P.; Hamajima, A.; Kira, K.; Isobe, M. Synlett 2002, 588.
37. Lee, H.-Y.; An, M. Tetrahedron Lett. 2003, 44, 2775.
38. (a) Kira, K.; Tanda, H.; Hamajima, A.; Baba, T.; Takai, S.; Isobe, M. Tetrahedron 2002, 58, 6485.
39. (b) Absence of BTMSA leads to further reduction of unsaturated ketone product to corresponding saturated carbonyl compound.
40. Fernandes-Megia, E.; Lay, S. V. Synlett 2000, 455.
41. Redlich, H.; Sudau, W.; Paulsen, H. Tetrahedron 1985, 41, 4253.
42. Burford, C.; Cooke, F.; Ehlinger, E.; Magnus, P. J. Am. Chem. Soc. 1977, 99, 4536.