Stereoselective Total Synthesis of (±)-Swainsonine Based on Endo Mode Cyclization

Journal of Organic Chemistry

Volumn 63, Issue 18, 1998, Pages 6281-6287

  Mukai, Chisato ^a   Sugimoto, Yu Ichi ^a   Miyazawa, Kana ^a   Yamaguchi, Sumie ^a   Hanaoka, Miyoji ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001515202     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980598h     Document Type: Article

References (42)

1. (a) Mukai, C.; Ikeda, Y.; Sugimoto, Y.; Hanaoka, M. Tetrahedron Lett. 1994, 35, 2179.
2. (b) Mukai, C.; Sugimoto, Y.; Ikeda, Y.; Hanaoka, M. Tetrahedron Lett. 1994, 35, 2183.
3. (c) Mukai, C.; Sugimoto, Y.; Ikeda, Y.; Hanaoka, M. J. Chem. Soc., Chem. Commun. 1994, 1161.
4. (d) Mukai, C.; Sugimoto, Y.; Ikeda, Y.; Hanaoka, M. Tetrahedron 1998, 54, 823.
5. (a) Guengerich, F. P.; DiMari, S. J.; Broquist, H. P. J. Am. Chem. Soc. 1973, 95, 2055.
6. (b) Schneider, M. J.; Ungemach, F. S.; Broquist, H. P.; Harris, T. M. Tetrahedron 1983, 39, 29.
7. Colegate, S. M.; Dorling, P. R.; Huxtable, C. R. Aust. J. Chem. 1979, 32, 2257.
8. Hino, M.; Nakayama, O.; Tsurumi, Y.; Adachi, K.; Shibata, T.; Terano, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiot. 1985, 38, 926.
9. (a) Tulsiani, D. R. P.; Harris, T. M.; Touster, O. J. Biol. Chem. 1982, 257, 7936.
10. (b) Kino, T.; Inamura, N.; Nakahara, K.; Kiyoto, S.; Goto, T.; Terano, H.; Kohsaka, M. J. Antibiot. 1985, 38, 936.
11. (c) Dennis, J. W. Cancer Res. 1986, 46, 5131.
12. (d) Humphries, M. J.; Matsumoto, K.; White, S. L.; Olden, K. Cancer Res. 1986, 46, 5215.
13. (e) Humphries, M. J.; Matsumoto, K.; White, S. L.; Molyneux, R. J.; Olden, K. Cancer Res. 1986, 46, 5215.
14. (a) Ferreira, F.; Greek, C.; Genet, J. P. Bull. Soc. Chim. Fr. 1997, 134, 615.
15. (b) Hembre, E. J.; Pearson, W. H. Tetrahedron 1997, 53, 11021.
16. (c) Hunt, J. A.; Roush, W. R. J. Org. Chem. 1997, 62, 1112.
17. (d) Pearson, W. H.; Membre, E. J. J. Org. Chem. 1996, 61, 7217.
18. (e) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 5537.
19. (f) Zhou, W.-S.; Xei, W.-G.; Lu, Z.-H.; Pan, X.-F. J. Chem. Soc., Perkin Trans. 1 1995, 2599.
20. (g) Rang S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049.
21. (h) Oishi, T.; Iwakuma, T.; Hirama, M.; Ito, S. Synlett 1995, 404.
22. (i) Hunt, J. A.; Roush, W. R. Tetrahedron Lett 1995, 36, 501.
23. (j) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358.
24. (k) For a recent review see, Takahata, M.; Momose, T. The Alkaloids 1993, 44, 189.
25. (l) Jirousek, M. R.; Cheung, A. W. H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. M. Tetrahedron Lett. 1993, 34, 3671.
26. (m) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org, Chem. 1993, 58, 3397.
27. (n) Gonzalez, F. B.; Barba, A. L.; Espina, M. R. Bull. Chem. Soc. Jpn. 1992, 65, 567.
28. (o) Pearson, W. H.; Lin, K.-C. Tetrahedron Lett. 1990, 31, 7571.
29. (p) Takahata, H.; Banba, Y.; Momose, T. Tetrahedron: Asymmetry 1990, 1, 763.
30. (q) Ikota, N.; Hanaki, A. Chem. Pharm. Bull. 1990, 38, 2712.
31. (r) Miller, S. A.; Chamberlin, A. R. J. Am. Chem. Soc. 1990, 112, 8100.
32. (s) Carpenter, N. M.; Fleet, G. W. J.; Cenci di Bello, I.; Winchester, B.; Fellows, L. E.; Nash, R. Tetrahedron Lett. 1989, 30, 7261.
33. (t) Bennett, R. B., III.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580.
34. (u) Dener, J. M.; Hart, D. J.; Ramesh, S. J. Org. Chem. 1988, 53, 602.
35. Mitsunobu, O. Synthesis 1981, 1.
36. Wolff, H. Org. React. 1946, 3, 307.
37. -1. A colorless prisms crystal, ca. 0.4 × 0.4 × 0.1 mm, was mounted on a glass fiber. All measurements were made on a Rigaku AFC5R diffractometer. The cell dimensions and intensities were refined by the least-squares method, using 25 reflections on the diffractometer with Mo Kα radiation with ω-scan mode for 2θ less than 55.0°. The structure was solved by direct method (MITHRIL method). The final cycle of full-matrix least-squares refinement was based on 2525 observed reflections. The final R value was 0.052.
38. (a) Ji, S.; Gortler, L. B.; Waring, A.; Battisti, A.; Bank, S.; Closson, W. D. J. Am. Chem. Soc. 1967, 89, 5311.
39. (b) McIntosh, M. J.; Matassa, L. J. Org. Chem. 1988, 53, 4452.
40. (a) Rassu, G.; Casiraghi, G.; Pinna, L.; Spanu, P.; Ulgheri, F. Tetrahedron 1993, 49, 6627.
41. (b) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397.
42. VanRheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 1973.