Metal-oxo induced syn-oxidative polycyclizations of hydroxypolyenes: Biomimetic synthesis of polycyclic ether natural products

Pure and Applied Chemistry

Volumn 70, Issue 2, 1998, Pages 355-358

  McDonald, Frank E ^a   Towne, Timothy B ^a   Schultz, Colleen C ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000019365     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac199870020355     Document Type: Article

References (27)

1. (a) Westley, J. W. In Antibiotics; Corcoran, J. W., Ed.; Springer-Verlag: New York, 1981; Vol. 4, pp 41-73.
2. (b) Dobler, M. Ionophores and Their Structures ; Wiley: New York, 1981.
3. (a) Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 275.
4. (b) Ahammadsahib, K. I.; Hollingworth, R. M.; McGovren, J. P.; Hui, Y.-H.; McLaughlin, J. L. Life Sci. 1993, 53, 1113.
5. Gu, Z.-M.; Fang, X.-P.; Zeng, L.; McLaughlin, J. L. Tetrahedron Lett. 1994, 35, 5367.
6. Cane, D. E.; Liang, T.-C.; Hasler, H. J. Am. Chem. Soc. 1982, 104, 7274.
7. Cane, D. E.; Celmer, W. D.; Westley, J. W. J. Am. Chem. Soc. 1983, 105, 3594.
8. (a) Townsend, C. A.; Basak, A. Tetrahedron 1991, 2591.
9. (b) Koert, U. Angew. Chem. Int. Ed. 1995, 34, 298.
10. For an overview of stereoinduction parameters for vanadium-catalyzed epoxidation of hydroxyalkenes, see: Hashimoto, M.; Harigaya, H.; Yanagiya, M.; Shirahama, H. J. Org. Chem. 1991, 56, 2299.
11. (a) Baskaran, S.; Islam, I.; Chandrasekaran, S. J. Chem. Res., Miniprint 1992, 2213.
12. (b) Schlecht, M. F.; Kim, H.-J. J. Org. Chem. 1989, 54, 583; and references therein.
13. (a) Tang, S.; Kennedy, R. M. Tetrahedron Lett. 1992, 33, 5299 and 5303.
14. (b) Sinha, S. C.; Sinha-Bagchi, A.; Keinan, E. J. Am. Chem. Soc. 1995, 117, 1447.
15. McDonald, F. E.; Towne, T. B. J. Am. Chem. Soc. 1994, 116, 7921.
16. Herrmann, W. A.; Thiel, W. R.; Kühn, F. E.; Fischer, R. W.; Kleine, M.; Herdtweck, E.; Scherer, W.; Mink, J. Inorg. Chem. 1993, 32, 5188.
17. McDonald, F. E.; Towne, T. B. J. Org. Chem. 1995, 60, 5750.
18. Kocienski, P.; Barber, C. Pure Appl. Chem. 1990, 62, 1933.
19. Review: Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
20. Andersson, P. G.; Sharpless, K. B. J. Am. Chem. Soc. 1993, 115, 7047.
21. (a) Walba, D. M.; Stoudt, G. S. Tetrahedron Lett. 1982, 23, 727.
22. (b) Corey, E. J.; Ha, D.-C. Tetrahedron Lett. 1988, 29, 3171.
23. Gemal, A. L.; Luche, J.-L. J. Am. Chem. Soc. 1981, 103, 5454.
24. McDonald, F. E.; Schultz, C. C., submitted for publication.
25. Johnson, W. S.; Werthemann, L.; Bartlett, W. R.; Brocksom, T. J.; Li, T.-T.; Faulkner, D. J.; Peterson, M. R. J. Am. Chem. Soc. 1970, 92, 741.
26. Takahashi, H.; Kawakita, T.; Yoshioka, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 7095.
27. Towne, T. B.; McDonald, F. E., submitted for publication.