Efficient construction of 8-membered ring framework of vinigrol through SmI2-induced coupling cyclization

Tetrahedron

Volumn 55, Issue 50, 1999, Pages 14369-14380

  Matsuda, Fuyuhiko ^a   Kito, Makoto ^a   Sakai, Toshinari ^a   Okada, Naoko ^a   Miyashita, Masaaki ^a   Shirahama, Haruhisa ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; UNCLASSIFIED DRUG; VINIGROL;

ARTICLE; CYCLIZATION; DRUG CONFORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL;

EID: 0033544804     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00885-6     Document Type: Article

References (40)

1. (a) Uchida, I; Ando, T.; Fukami, N.; Yoshida, K.; Hashimoto, M.; Toda, T.; Koda, S.; Morimoto, Y. J. Org. Chem. 1987, 52, 5292.
2. (b) Ando, T.; Tsurumi, Y.; Ohata, N.; Uchida, I.; Yoshida, K.; Okuhara, M. J. Antibiot. 1988, 41, 25.
3. (c) Ando, T.; Yoshida, K.; Okuhara, M. J. Antiblot. 1988, 41, 31.
4. Norris, D. B.; Depledge, P.; Jackson, A. P. PCT Int. Appl. WO 9107,953; Chem. Abstr. 1991, 115, 64776h.
5. Norris, D. B.; Depledge, P.; Jackson, A. P. PCT Int. Appl. WO 9107,953; Chem. Abstr. 1991, 115, 64776h.
6. (a) Devaux, J.-F.; Hanna, I.; Lallemand, J.-Y. J. Org. Chem. 1993, 58, 2349.
7. (b) Devaux, J.-F.; Hanna, I.; Lallemand, J.-Y.; Frangé, T. J. Chem. Res. (S) 1996, 32.
8. (c) Devaux, J.-F.; Hanna, I.; Lallemand, J.-Y. J. Org. Chem. 1997, 62, 5062.
9. (d) Mehta, G.; Reddy, K. S. Synlett 1996, 625.
10. 2) has become an exceedingly useful reagent for promoting reductive coupling reactions. For reviews, see: (a) Kagan, H. B. New J. Chem. 1990, 14, 453.
11. (b) Molander, G. A. Chem. Rev. 1992, 92, 2 9.
12. (c) Molander, G. A.; Harris, R. H. Chem. Rev. 1996, 96, 307.
13. 2-promoted Reformatsky reactions, ketyl-olefin reductive couplings, and pinacol couplings have been adapted to permit construction of medium ring molecules. See: (a) Tabuchi, T.; Kawamura, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 3889.
14. (b) Inanaga, J.; Yokoyama, Y.; Handa, Y.; Yamaguchi, M. Tetrahedron Lett 1991 32, 6371.
15. (c) Molander, G. A.; McKie, J. A. J. Org. Chem. 1992, 57, 3132.
16. (d) Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186.
17. (e) Shiina, I.; Uoto, K.; Mori, N.; Kosugi, T.; Mukaiyama, T. Chem. Lett. 1995, 181.
18. (f) Swindell, C. S.; Fan, W. Tetrahedron Lett. 1996, 37, 2321.
19. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391.
20. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158.
21. (c) Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111.
22. (d) Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532.
23. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900.
24. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729.
25. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 55, 987.
26. (h) Kawatsura, M.; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373.
27. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett 1996, 1057.
28. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett 1997, 479.
29. 2-promoted ketyl-olefin coupling. See: Ref. 6i.
30. For a preliminary account of part of this work, see: Kito, M.; Sakai, T.; Miyashita, M.; Shirahama, H.; Matsuda, F. Synlett 1997, 219.
31. Hegde, S. G.; Bechwith, D.; Doti, R.; Wolinsky, J. J. Org. Chem. 1985, 50, 894.
32. Martinelli, M. J. J. Org. Chem. 1990, 55, 5065.
33. 2-induced reactions benefit from the presence of HMPA. See: (a) Otsubo, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 5763.
34. (b) Inanaga, J.; Ishikawa, M.; Yamaguchi, M. Chem. Lett. 1987, 1485.
35. (c) Otsubo, K.; Kawamura, K.; Inanaga, J.; Yamaguchi, M. Chem. Lett. 1987, 1487.
36. (d) Otsubo, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 4437.
37. The model acetate 11c was subjected to a Monte Carlo conformational search procedure in MacroModel (Version 6.0) equipped with the MM2 force field. The calculations found the 5 conformers within 3 kcal/mol of the ground state. The structures of the bicyclo [1.3.5] undecane ring systems of the higher energy 4 conformers are closely related to that of the bicyclic ring system of the lowest energy conformer 1c-A. Furthermore, the same MM2 calculations performed on the model alcohol 3c (Figure 1) indicated that there are 2 conformers within 3 kcal/mol of the global minimum. The conformational features of the 2 conformers are the same as those of the 5 conformers of 11c. We are grateful to Dr. Kazuhiko Nakatani (Kyoto University) for his help in performing the MM2 calculations.
38. 1,3 strain), see: Johnson, F. Chem. Rev. 1968, 68, 375.
39. 1 methine proton is always detected as a broad singlet.
40. 2-promoted cyclization of medium rings (8- and 9-membered carbocycles) in general. See: Matsuda, F.; Sakai, T.; Okada, N.; Miyashita, M. Tetrahedron Lett. 1998, 39, 863.