New strategy for convergent synthesis of trans-fused polyether frameworks based on palladium-catalyzed Suzuki cross-coupling reaction

Tetrahedron Letters

Volumn 39, Issue 49, 1998, Pages 9027-9030

  Sasaki, Makoto ^a   Fuwa, Haruhiko ^a   Inoue, Masayuki ^a   Tachibana, Kazuo ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; POLYETHER DERIVATIVE;

ARTICLE; CATALYSIS; CONFORMATIONAL TRANSITION; CROSS REACTION; STRUCTURE ANALYSIS; SYNTHESIS;

LATEOLABRAX JAPONICUS;

EID: 0032481078     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02025-5     Document Type: Article

References (31)

1. 1. Structures: (a) Lin, Y.-Y.; Risk, M.; Ray, S. M.; Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773-6775.
2. (b) Shimizu, Y.; Chou, H.-N.; Van Duyne, G.; Clardy, J. C. J. Am. Chem. Soc. 1986, 108, 514-515.
3. (c) Lee, M. S.; Repeta, D. J.; Nakanishi, K.; Zagorski, M. G. J. Am. Chem. Soc. 1986, 108, 7855-7856.
4. 2. Total synthesis of brevetoxin B: Nicolaou, K. C.; Rutjes, F. P. J. T.; Theodorakis, E. A.; Tiebes, J.; Sato, M.; Untersteller, E. J. Am. Chem. Soc. 1995, 117, 10252-10263 and references cited therein. Total synthesis of brevetoxin A: Nicolaou, K. C.; Yang, Z.; Shi, G.-q.; Gunzner, J. L.; Agrios, K. A.; Gartner, P. Nature, 1998, 392, 264-269.
5. 2. Total synthesis of brevetoxin B: Nicolaou, K. C.; Rutjes, F. P. J. T.; Theodorakis, E. A.; Tiebes, J.; Sato, M.; Untersteller, E. J. Am. Chem. Soc. 1995, 117, 10252-10263 and references cited therein. Total synthesis of brevetoxin A: Nicolaou, K. C.; Yang, Z.; Shi, G.-q.; Gunzner, J. L.; Agrios, K. A.; Gartner, P. Nature, 1998, 392, 264-269.
6. 3. (a) Murata, M.; Legrand, A.-M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386.
7. (b) Satake, M.; Murata, M.; Yasumoto, T. Tetrahedron Lett. 1993, 34, 1975-1976.
8. (c) Satake, M.; Ishibashi, Y.; Legrand, A.-M.; Yasumoto, T. Biosci. Biochem. Biotech. 1996, 60, 2103-2105.
9. (d) Satake, M.; Morohashi, A.; Oguri, H.; Oishi, T.; Hirama, M.; Harada, N.; Yasumoto, T. J. Am. Chem. Soc. 1997, 119, 11325-11326.
10. (e) Satake, M.; Fukui, M.; Legrand, A.-M; Cruchet, P.; Yasumoto, T. Tetrahedron Lett. 1998, 39, 1197-1198.
11. 4. (a) Murata, M.; Naoki, H.; Matsunaga, S.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1994, 116, 7098-7107.
12. (b) Nonomura, T.; Sasaki, M.; Matsumori, N.; Murata, M.; Tachibana, K. Yasumoto, T. Angew. Chem. Int. Ed. Engl. 1996, 35, 1675-1678 and references cited therein.
13. (c) Zheng, W.; DeMattei, J. A.; Wu, J.-P.; Duan, J. J.-W.; Cook, L. R. Oinuma, H.; Kishi, Y. J. Am. Chem. Soc. 1996, 118, 7946-7968.
14. (d) Cook, L. R.; Oinuma, H.; Semones, M. A.; Kishi, Y. ibid. 1997, 119, 7928-7937.
15. 5. For a recent review on marine toxins, see: Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897-1909.
16. 6. For a recent review on polyether synthesis, see: E. Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Martín, J. D. Chem. Rev. 1995, 95, 1953-1980.
17. 7. Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565-1566.
18. 8. (a) Miyaura, N.; Ishiyama, T.; Sasaki, T.; Ishikama, M.; Satoh, M.; Suzuki, A. J. Am. Chem. Soc. 1984, 111, 314-321.
19. (b) Oh-e, T.; Miyaura, N.; Suzuki, A. J. Org. Chem. 1993, 58, 2201-2208.
20. (c) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
21. 9. (a) Johnson, C. R.; Braun, M. P. J. Am. Chem. Soc. 1993, 115, 11014-11015.
22. (b) Johns, B. A.; Pan, Y. T.; Elbein, A. D.; Johnson, C. R. J. Am. Chem. Soc. 1997, 119, 4856-4865.
23. (c) Meng, D.; Bertinato, P.; Balog, A.; Su, D.-S.; Kamenecka, T.; Sorensen, E. J.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10073-10092.
24. 10. (a) Inoue, M.; Sasaki, M.; Tachibana, K. Angew. Chem. Int. Ed. Engl. 1998, 37, 965-969.
25. (b) Sasaki, M.; Inoue, M.; Noguchi, T.; Takeichi, A.; Tachibana, K. Tetrahedron Lett. 1998, 39, 2783-2786.
26. 11. (a) Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611-3613.
27. (b) Pine, S. H.; Zahler, R.; Evans, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 3270-3274.
28. 12. Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392-6394.
29. 13. Alvarez, E.; Pérez, R.; Rico, M.; Rodriguez, R. M.; Martín, J. D. J. Org. Chem. 1996, 61, 3003-3016.
30. 3As as a coligand had a significant positive effect on palladium(0)-catalyzed cross-coupling reaction, see: (a) Farina, V.; Krishman, B. J. Am. Chem. Soc. 1991, 113, 9585-9595.
31. (b) Kojima, A.; Honzawa, S.; Boden, C. D. J.; Shibasaki, M. Tetrahedron Lett. 1997, 38, 3455-3458.