Efficient synthesis of bicyclic lactones via tungsten-mediated intramolecular cycloalkenation

Journal of Organic Chemistry

Volumn 63, Issue 21, 1998, Pages 7289-7293

  Liang, Kwei Wen ^a   Chandrasekharam, Malapaka ^a   Li, Chien Le ^a   Liu, Rai Shung ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000095038     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980728m     Document Type: Article

References (37)

1. Bruce, M. I. Chem. Rev. 1991, 91, 257.
2. (a) Davidson, A.; Solar, J. P. J. Organomet. Chem. 1979, 166, C13.
3. (b) Abbott, S.; Davies, S. G.; Warner, P. J. Organomet. Chem. 1983, 246, C65.
4. (c) Consiglio, G.; Baangerter, F.; Darpin, C.; Morandini, F.; Lucchini, V. Organometallics 1984, 3, 1446.
5. (a) Liang, K.-W.; Li, W.-T.; Peng, S.-M.; Wang, S.-L.; Liu, R.-S. J. Am. Chem. Soc. 1997, 119, 4404.
6. (b) Chang, S.-T.; Chandrasekharam, M.; Liang, K.-W. Li, W.-T.; Liu, R.-S. Tetrahedron. Lett. 1998, 39, 643.
7. Konig, K.; Neumann, W. P. Tetrahedron Lett. 1967, 495.
8. (a) Deleris, G.; Dunogues, J.; Calas, R. J. Organomet. Chem. 1975, 936, 43.
9. (b) Kuwajima, I.; Nakamura, E.; Hashimoto, K. Tetrahedron 1983, 39, 975.
10. (c) Yamamoto, Y.; Nishi, S.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1986, 102.
11. (a) Lozar, L. D.; Clark, R. D.; Heathcock, C. H. J. Org. Chem. 1977, 42, 1386.
12. (b) Johnson, W. S.; Yarnell, T. M.; Myers, R. F.; Morton, D. R. Tetrahedron Lett. 1978, 26, 3201.
13. (c) Johnson, W. S.; Yarnell, T. M.; Myers, R. F.; Morton, D. R.; Boots, D. R. J. Org. Chem. 1980, 45, 1254.
14. For review papers of saturated and unsaturated lactones, see the representative examples: (a) Hoffman, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94.
15. (b) Grieco, P. A. Synthesis 1975, 67.
16. (c) Collins, I. Contemp. Org. Syn. 1997, 4, 281.
17. (d) Tietze, L.-F. Angew. Chem., Int. Ed. Engl. 1983, 22, 828.
18. (e) Demuth, M.; Schaffner, K. Angew. Chem., Int. Ed. Engl., 1982, 21, 820.
19. (a) Ohta, H.; Kobori, T.; Fujisawa, T. J. Org. Chem. 1977, 42, 1231.
20. (b) Amri, H.; Rambaud, M.; Villieras, J. Tetrahedron 1990, 46, 3535.
21. (c) Yamane, T.; Takahashi, M.; Ogasawara, K. Synthesis 1994, 444.
22. (a) Sakan, T.; Murai, F.; Isoe, S.; BeHyeon, S.; Hayashi, Y. J. Chem. Soc. Jpn., Pure Chem. Sect. 1969, 90, 507.
23. (b) Ellis, J. J.; Stodola, F. H.; Vesonder, R. F.; Glass, C. A. Nature 1964, 203, 1382.
24. Feldman, K. S.; Bruendl, M. M.; Schildknegt, K.; Bohnstedt, A. C. J. Org. Chem. 1996, 61, 5440.
25. Bruce, M. L.; Humphrey, M. G.; Mattisons, J. G.; Roy, S. K.; Swincer, A. G. Aust. J. Chem. 1984, 1041.
26. w = 0.036. The X-ray data of 14 is provided in Supporting Information.
27. (a) Abbot, S.; Davies, S. G.; Warner, P. J. Organomet. Chem. 1983, 246, C65.
28. (b) Gamasa, M. P.; Gimeno, J.; Lastra, E.; Martin, B. M.; Anillo, A.; Tiripicchio, A. Organometallics 1992, 11, 1373.
29. Douglas, B. E.; McDaniel, D. H.; Alexander, J. F. Concepts and Models of Inorganic Chemistry, 3rd ed.; John Wiley & Sons: New York, 1994; Chapter 7, p 309.
30. Bullock, R. M.; Song, J.-S. J. Am. Chem. Soc. 1994, 116, 8602.
31. Nugent, W. A.; Hobbs, F. W. J. Org. Chem. 1986, 51, 3376.
32. Amri, H.; Villieras, J. Tetrahedron Lett. 1987, 5521.
33. Fujisawa, T.; Ohta, H.; Kobori, T. J. Chem. Soc., Chem. Commun. 1976, 186.
34. Hays, D. S.; Fu, G. F. J. Org. Chem. 1997, 62, 7070.
35. Mahoney, W. S.; Stryker, J. M. J. Am. Chem. Soc. 1989, 111, 1818.
36. Bezman, S. A.; Churchill, M. R.; Osborn J. A.; Wormald, M. J. Am. Chem. Soc. 1971, 93, 2063.
37. Goeden, G. V.; Caulton, K. G. J. Am. Chem. Soc. 1981, 103, 7354.