Synthetic studies of halichondrin B, an antitumor polyether macrolide isolated from a marine sponge 5. A highly concise and efficient synthesis of the C37∼C54 tricyclic JKL-ring part

Heterocycles

Volumn 42, Issue 1, 1996, Pages 99-104

  Horita, Kiyoshi ^a   Hachiya, Shun Ichiro ^a   Ogihara, Kazuhito ^a   Yoshida, Yutaka ^a   Nagasawa, Masaaki ^a   Yonemitsu, Osamu ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

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[No Author keywords available]

Indexed keywords

EID: 0002903462     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-95-S30     Document Type: Article

References (38)

1. (a) D. Uemura, K. Takahashi, T. Yamamoto, C. Katayama, J. Tanaka, Y. Okumura, Y. Hirata, J. Am Chem. Soc., 1985, 107, 4796.
2. (b) Y. Hirata, D. Uemura, Pure Apple Chem., 1986, 58, 701.
3. (a) T. D.Aicher, Y. Kishi, Tetrahedron Lett., 1987, 28, 3463.
4. (b) Y. Kishi, Pure Apple Chem., 1992, 64, 343.
5. (c) T. D. Aicher, K. R. Buszek, F. G. Fang, C. T. Forsyth, S. H. Jung, Y. Kishi, P. M. Scola, Tetrahedron Lett., 1992, 33, 1549.
6. (d) K. R. Busaek, F. G. Fang, C. J. Forsyth, S. H. Jung, Y. Kishi, P. M. Scola, S. K. Yoon, Tetrahedron Lett., 1992, 33, 1553.
7. (e) F. G. Fang, Y. Kishi, M. C. Matelich, P. M. Scola, Tetrahedron Lett., 1992, 33, 1557.
8. (f) T. D. Aicher, K. R. Buszek, F. G. Fang, C. J. Forsyth, S. H. Jung, Y. Kishi, M. C. Matelich, P. M. Scola, D. M. Spero, S. K. Yoon, J. Am Chem. Soc., 1992, 114, 3162.
9. (g) J.-W. J. Duran, Y. Kishi, Tetrahedron Lett., 1993, 34, 7531.
10. (h) S. Kim, R. G. Salomon, Tetrahedron Lett., 1989, 30, 6279.
11. (i) A. J. Cooper, R. G. Salomon, Tetrahedron Lett., 1990, 31, 3813.
12. (j) E. DiFranco, V. T. Ravikumar, R. G. Salomon, Tetrahedron Lett., 1993, 34, 3247.
13. (k) S. D. Burke, J. L. Buchanan, J. D. Rovin, Tetrahedron Lett., 1991, 52, 3961.
14. (1) S. D. Burke, K. W. Jung, J. R. Phillips, R. E. Perri, Tetrahedron Lett., 1994, 35, 703.
15. (a) K. Horita, S. Hachiya, M. Nagasawa, M. Hikota, O. Yonemiteu, Synlett, 1994, 38.
16. (b) K. Horita,; M. Nagasawa, S. Hachiya, O. Yonemitsu, Synlett, 1994, 40.
17. (c) K. Horita, Y. Sakurai, M. Nagasawa, S. Hachiya, O. Yonemitsu, Synlett, 1994, 43.
18. (d) K. Horita, Y. Sakurai, M. Nagasawa, K. Maeno,; S. Hachiya, O. Yonemiysu, Synlett, 1994, 46.
19. 2J chemical equations presented.
20. K. Horita, Y. Sakurai, S. Hachiya, M. Nagasawa, O. Yonemiteu, Chem. Pharm. Bull., 1994, 42, 683.
21. (a) F. E. Ziegler, P. J. Gilligan, J. Org. Chem., 1981, 46, 3874.
22. (b) K. C. Nicolaou, M. R. Pavia, S. P. Seitz, J. Am. Chem. Soc., 1981, 103, 1224.
23. (c) W. R. Roush, B. M. Lesur, Tetrahedron Lett., 1983, 24, 2231.
24. (d) W. R. Roush, M. R. Michaelides, D. F. Tai, B. M. Lesur, W. K. M. Chong, D. D. Harris, J. Am. Chem. Soc., 1989, 111, 2984.
25. (e) D. B. Miller, S. R. Raychaudhuri, K. Avasthi, K. Kak, B. Levision, R. G. Salomom, J. Org. Chem., 1990, 55, 3164.
26. (f) H. Nemoto, M. Ando, K. Fukumoto, Tetrahedron Lett., 1990, 31, 6205.
27. (g) S. Hanessian, K. Sumi, Synthesis, 1991, 1083.
28. (h) Y. Yamamoto, Y. Chouman, S. Nishi, T. Ibuka, H. Kitahara, J. Am. Chem. Soc., 1992, 114, 7652.
29. Unless otherwise noted, numbering is based on those of halichondrin B (1).
30. 1H-NOESY ) after conversion of 10 to the six membered lactone (18) via the conventional 3 steps, as shown below. chemical equations presented.
31. E. J. Corey, G. T. Kwiatowski, J. Am Chem. Soc., 1966, 88, 5654.
32. A. J. Mancuso, D. Swern, Synthesis, 1981, 165.
33. 3); δ 18.16, 30.93, 35.24, 37.94, 55.34, 58.83, 68.52, 74.99, 78.60, 96.84, 113.66, 129.86, 130.92, 159.25.
34. 1BuOK, the silylation reaction didn't proceed at all.
35. 1BuOK, the silylation reaction didn't proceed at all.
36. nhexane=1 : 2).
37. (a) K.-M. Chen, G. E. Hardtmann, K. Prasad, O. Repic, M. J. Shapiro, Tetrahedron Lett., 1987, 28, 155.
38. (b) D. A. Evans, A. H. Hoveyda, K. Narasaka, F. C. Pai, Tetrahedron, 1987, 43, 2233.