Convergent Synthesis of the E′FGH′ Ring Fragment of Ciguatoxin 1B via an Acetylene Cobalt Complex Strategy

Organic Letters

Volumn 4, Issue 7, 2002, Pages 1183-1186

  Takai, Shigeyuki ^a   Isobe, Minoru ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; BETA LACTAMASE; CIGUATOXIN; CIGUATOXIN 1B (CTX 1B); COBALT; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; MARINE TOXIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; SYNTHESIS;

ACETYLENE; BETA-LACTAMASES; CIGUATOXINS; COBALT; INDICATORS AND REAGENTS; MARINE TOXINS; MODELS, MOLECULAR; MOLECULAR CONFORMATION;

EID: 0037018464     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0256264     Document Type: Article

References (50)

1. (a) Scheuer, P. J.; Takahashi, W.; Tsutsumi, J.; Yoshida, T. Science 1967, 155, 1267-1268.
2. (b) Murata, M.; Legurand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386.
3. (c) Satake, M.; Morohashi, A.; Oguri, H.; Oishi, T.; Hirama, M.; Harada, N.; Yasumoto, T. J. Am. Chem. Soc. 1997, 119, 11325-11326.
4. (d) Yasumoto, T. Chem. Rec. 2001, 1, 228-242.
5. (a) Hirama, M.; Oishi, T.; Uehara, H.; Inoue, M.; Maruyama, M.; Oguri, H.; Satake, M. Science 2001, 294, 1904-1907.
6. (b) Takakura, H.; Noguchi, K.; Sasaki, M.; Tachibana, K. Angew. Chem., Int. Ed. 2001, 40, 1090-1093.
7. (c) Fujiwara, K.; Takaoka, D.; Kusumi, K.; Kawai, K.; Murai, A. Synlett 2001, 691-693.
8. (d) Eriksson, L.; Guy, S.; Perlmutter, P. J. Org. Chem. 1999, 64, 8396-8398.
9. (e) Leeuwenburgh, M. A.; Kulker, C.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H. Synlett 1999, 1945-1947.
10. (f) Ravelo, J. D.; Regueiro, A.; Roddriguez, E.; Vera, J.; Martin, J. D. Tetrahedron Lett. 1996, 37, 2869-2872.
11. (g) Soler, M. A.; Palazon, J. M.; Martin, V. S. Tetrahedron Lett. 1993, 34, 5471-5474 and references therein.
12. (a) Isobe, M.; Yenjai, C.; Tanaka, S. Synlett 1994, 11, 916-918.
13. (b) Yenjai, C.; Isobe, M. Tetrahedron 1998, 54, 2509-2520.
14. (c) Isobe, M.; Hosokawa, S.; Kira, K. Chem. Lett. 1996, 473-474.
15. (d) For a review, see; Isobe, M.; Nishizawa, R.; Hosokawa, S.; Nishikawa, T. Chem. Commun. 1998, 2665-2676.
16. (a) Hosokawa, S.; Isobe, M. Tetrahedron Lett. 1998, 39, 2609-2612.
17. (b) Shibuya, S.; Isobe, M. Tetrahedron 1998, 54, 6677-6698.
18. (a) Kira, K.; Isobe, M. Chem. Lett. 2001, 432-433.
19. (b) Kira, K.; Hamajima, A.; Isobe, M. Tetrahedron 2002, 58, 1875-1888.
20. (a) Isobe, M.; Kitamura, M.; Goto, T. Tetrahedron Lett. 1979, 3465-3468.
21. (b) Isobe, M.; Funabashi, Y.; Ichikawa, Y.; Mio, S.; Goto, T. Tetrahedron Lett. 1984, 25, 2021-2024.
22. (c) Isobe, M. New Synthetic Methods Using Vinyl Sulfones-Developments in Heteroconjugate Addition. In Perspectives in the Organic Chemistry of Sulfur; Zwanenburg, B., Klunder, A. J. H., Eds.; Studies in Organic Chemistry, 1987; Vol. 28, pp 209-229.
23. (c) Isobe, M. New Synthetic Methods Using Vinyl Sulfones-Developments in Heteroconjugate Addition. In Perspectives in the Organic Chemistry of Sulfur; Zwanenburg, B., Klunder, A. J. H., Eds.; Studies in Organic Chemistry, 1987; Vol. 28, pp 209-229.
24. (a) Hosokawa, S.; Isobe, M. Synlett 1995, 1179-1180.
25. (b) Hosokawa, S.; Isobe, M. Synlett 1996, 351-352.
26. (c) Hosokawa, S.; Isobe, M. J. Org. Chem. 1999, 64, 37-48.
27. (d) Saeeng, R.; Isobe, M. Tetrahedron Lett. 1999, 40, 1911-1914.
28. (e) Saeeng, R.; Isobe, M. Heterocycles 2001, 54, 789.
29. Kira, K.; Isobe, M. Tetrahedron Lett. 2001, 42, 2821-2824.
30. Kira, K.; Isobe, M. Tetrahedron Lett. 2000, 41, 5951-5955.
31. (a) Liu, T.-Z.; Isobe, M. Synlett 2000, 587-589.
32. (b) Liu, T.-Z.; Isobe, M. Tetrahedron 2000, 56, 5391-5404.
33. (c) Liu, T.-Z.; Li, J.-M.; Isobe, M. Tetrahedron 2000, 56, 10209-10219.
34. (d) Liu, T.-Z.; Isobe, M. Synlett 2000, 266-268.
35. Synthesis of another model system of the EFGH ring: (a) Sasaki, M.; Noguchi, T.; Tachibana, K. Tetrahedron Lett. 1999, 40, 1337-1340.
36. (b) Imai, H.; Uehara, H.; Inoue, M.; Oguri, H.; Oishi, T.; Hirama, M. Tetrahedron Lett. 2001, 42, 6219-6222.
37. 3CN; (5) TBSCl, imidazole, DMF.
38. Corey, E. J.; Ruker, C. Tetrahedron Lett. 1982, 23, 719-722.
39. Isobe, M.; Tsukiyama, T. Tetrahedron Lett. 1992, 33, 7911-7914.
40. Gemal, A.; Luche, J. L. J. Am. Chem. Soc. 1981, 103, 5454-5459.
41. Tanaka, S.; Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1993, 34, 5757-5760.
42. (a) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974-5976.
43. (b) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780.
44. (a) Hartman, C.; Meyer, V. Chem. Ber. 1893, 26, 1727.
45. (b) Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537-4538.
46. McCauley J. A.; Nagasawa, K.; Lander, P. A.; Mischke, S. G.; Semones, M. A.; kishi, Y. J. Am. Chem. Soc. 1998, 120, 7647-7648.
47. Kira, K.; Isobe, M. J. Synth. Org. Chem., Jpn. 2000, 58, 23-30.
48. Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978.
49. (a) Inoue, M.; Sasaki, M., Tachibana, K. Tetrahedron Lett. 1997, 38, 1611-1614.
50. (b) Inoue, M.; Sasaki, M.; Tachibana, K. Terahedron 1999, 55, 10949-10970.