Olefin metathesis reactions of some aromatic dienes with ortho- and meta-disubstitution. Formation of 10-, 12-, 14-, and 17-membered cyclic compounds and isomerization of an allylic alcohol

Heterocycles

Volumn 53, Issue 2, 2000, Pages 301-314

  Nakashima, Katsuyuki ^a   Ito, Rika ^a   Sono, Masakazu ^a   Tori, Motoo ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKENE DERIVATIVE; ALLYL ALCOHOL; PHENYL GROUP; POLYMER; VINYL DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ISOMERISM; SYNTHESIS;

EID: 0034141369     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-8754     Document Type: Article

References (36)

1. R. H. Grubbs, S. J. Miller, and G. C. Fu, Acc. Chem. Res., 1995, 28, 446.
2. H.-G. Schmalz, Angew. Chem., Int. Ed. Eng., 1995, 34, 1833.
3. P. Schwab, R. H. Grubbs, and J. W. Ziller, J. Am. Chem. Soc., 1996, 118, 100.
4. A. Fürstner and K. Langemann, Synthesis, 1997, 792.
5. M. Schuster and S. Blechert, Angew. Chem., Int. Engl., 1997, 36, 2036.
6. R. H. Grubbs and S. Chang, Tetrahedron, 1998, 54, 4413.
7. S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1, 1998, 371.
8. (a) T. Kirkland and R. H. Grubbs, J. Org. Chem., 1997, 62, 7310.
9. (b) C. F. Sturino and J. C. Y. Wong, Tetrahedron Lett., 1998, 39, 9623.
10. (a) A. Fürstner and T. Müller, Synlett., 1997, 1010.
11. (b) A. Fürstner, M. Piquet, C. Bruneau, and P. H. Dixneuf, Chem. Commun., 1998, 1315.
12. T. Oishi, Y. Nagumo, and M. Hirama, Chem. Commun., 1998, 1041.
13. K. Gerlach, M. Quitschalle, and M. Kalesse, Tetrahedron Lett., 1999, 40, 3553.
14. S. Chang and R. H. Grubbs, Tetrahedron Lett., 1997, 38, 4757.
15. A. G. M. Barrett, S. P. D. Baugh, D. C. Braddock, K. Flack, V. C. Gibson, M. R. Giles, E. L. Marshall, P. A. Procopiou, A. J. P. White, and D. J. Williams, J. Org. Chem., 1998, 63, 7893.
16. M. Delgado and J. D. Martín, J. Org. Chem., 1999, 64, 4798.
17. M. Tori, A. Aiba, and K. Nakashima, unpublished results.
18. (a) M. Nagai, M. Kubo, M. Fujita, T. Inoue, and M. Matsuo, Chem. Commun., 1976, 338.
19. (b) S. Nagumo, N. Kaji, T. Inoue, and M. Nagai, Chem. Pharm. Bull., 1993, 41, 1255.
20. (c) S. Nagumo, S. Ishizawa, M. Nagai, and T. Inoue, Chem. Pharm. Bull., 1996, 44, 1086.
21. (d) G. I. Gonzalez and J. Zhu, J. Org. Chem., 1997, 62, 7544.
22. (e) G. I. Gonzalez and J. Zhu, J. Org. Chem., 1999, 64, 914.
23. R. Breitenbach, C. K.-F. Chiu, S. S. Massett, M. Meltz, C. W. Murtiashaw, S. L. Pezzullo, and T. Staigers, Tetrahedron: Asymmetry, 1996, 7, 435.
24. D. Joe and L. Overman, Tetrahedron Lett., 1997, 38, 8635. In this report, the isomerization of the double bond into the more substituted position was observed.
25. T. R. Hoye and H. Zhao, Org. Lett., 1999, 1, 169.
26. A. G. M. Barrett, S. P. D. Baugh, D. C. Braddock, K. Flack, V. C. Gibson, M. R. Giles, E. L. Marshall, P. A. Procopiou, A. J. P. White, and D. J. Williams, J. Org. Chem., 1998, 63, 7893.
27. S. Chang and R. H. Grubbs, J. Org. Chem., 1998, 63, 864.
28. P. Wipf and W. S. Weiner, J. Org. Chem., 1999, 64, 5321.
29. (a) J. P. A. Harrity, D. S. La, D. R. Cefalo, M. S. Visser, and A. H. Hoveyda, J. Am. Chem. Soc., 1998, 120, 2343.
30. (b) C. W. Johannes, M. S. Visser, G. S. Weatherhead, and A. H. Hoveyda, J. Am. Chem. Soc., 1998, 120, 8340.
31. (c) J. S. Kingsbury, J. P. A. Harrity, P. J. Bonitatebus, Jr., and A. H. Hoveyda, J. Am. Chem. Soc., 1999, 121, 791.
32. F. W. Wehrli and T. Nishida, 'Fortschritte der Chemie organischer Naturstoffe: The Use of Carbon-13 Nuclear Magnetic Resonance Spectroscopy in Natural Products Chemistry,' Vol. 36, ed. by L. Zechmeister, W. Herz, H. Grisebach, and G. W. Kirby, Springer-Verlag, Wien, New York, 1979, pp. 1-229.
33. C. F. Sturino and J. C. Y. Wong, Tetrahedron Lett., 1998, 39, 9623.
34. T. R. Hoye and H. Zhao, Org. Lett., 1999, 1, 1123.
35. M. Stefinovic and V. Snieckus, J. Org. Chem., 1998, 63, 2808.
36. O. Sellier, P. Van de Weghe, D. Le Nouen, C. Strehler, and J. Eustache, Tetrahedron Lett., 1999, 40, 853.