An Iterative Approach to Fused Ether Ring Systems

Journal of Organic Chemistry

Volumn 63, Issue 16, 1998, Pages 5310-5311

  Rainier, Jon D ^a   Allwein, Shawn P ^a  

^a University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000677383     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980996k     Document Type: Article

References (32)

1. Red Tides; Okaichi, T., Anderson, D. M., Nemoto, T., Ed.; Elsevier: New York, 1989.
2. Nagai, H.; Torigoe, K.; Satake, M.; Murata, M.; Yasumoto, J. J. Am. Chem. Soc. 1992, 114, 1102-1103.
3. Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem. 1992, 57, 7, 5448-5453.
4. 30-32
5. Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1996, 118, 8158-8159.
6. Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123-126.
7. Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127-130.
8. Bowman, J. L.; McDonald, F. E. J. Org. Chem. 1998, 63, 3680-3682.
9. Alvarez, E.; Diaz, M. T.; Ferez, R.; Ravelo, J. L.; Regueiro, A.; Vera, J. A.; Zurita, D.; Martin, J. D. J. Org. Chem. 1994, 59, 2848-2876.
10. Lemieux, R. U.; Huber, G. J. Am. Chem. Soc. 1956, 78, 4117-4119.
11. Bellosta, V.; Czernecki, S. J. Chem. Soc., Chem. Commun. 1989, 199-200.
12. Belosludtsev, Y. Y.; Bhatt, R. K.; Falck, J. R. Tetrahedron Lett. 1995, 33, 5881-5882.
13. Hanessian, S.; Liak, T. J.; Dixit, D. M. Carbohydr. Res. 1981, 88, C14-C19.
14. Danishefsky, S. J.; McClure, K. F.; Randolph, J. T.; Ruggeri, R. B. Science 1993, 260, 1307-1309.
15. Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661-6666.
16. Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452.
17. Despite the substantial work that has been accomplished in this area, there exists considerable room for improvement as the current state of the art involves the use of highly sensitive organometallic reagents, often in stoichiometric quantities. For a discussion of efficiency and organic synthesis, see: Trost, B. M. Science 1991, 254, 1471-1477.
18. Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 3800-3801.
19. Fujimura, O.; Fu, G. C.; Grubbs, R. H. J. Org. Chem. 1994, 59, 4029-4031.
20. Nicolaou, K. C.; Postema, M. H. D.; Yue, E. W.; Nadin, A. J. Am. Chem. Soc. 1996, 118, 10335-10336.
21. Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565-1566.
22. Barluenga, J.; Campos, P. J.; Gonzalez-Nunez, E.; Asensio, G. Synthesis 1985, 426-429.
23. Takai, K.; Kakiuchi, T.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1994, 59, 2668-2670.
24. Exposure of acetate 9 to the Tebbe or Petasis reagents has led only recovery of starting material or decomposition upon more vigorous reaction conditions (110 °C).
25. 2 resulted in only 15% of 11.
26. We believe that this is due to coordination of the four oxygens about the Pyran ring with Ti. Addition of more than 5 equiv of reagent resulted in the isolation of significant quantities of alcohol 7 after aqueous workup.
27. Thus far, we have been able to isolate 13 in 15% yield by extending the time of the reaction, completely decomposing enol ether 11 in the process. The major component from this preliminary experiment appears to be dimeric.
28. We have tentatively identified the only other recognizable product from this reaction as the exocyclic enol ether from deprotonation and epoxide opening. Thus far, We have been unable to determine the relative stereo-chemistry at the carbon bearing the hydroxyl group in this compound.
29. Marzabadi, C. H.; Spilling, C. D. J. Org. Chem. 1993, 58, 3761-3766.
30. Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Tiebes, J.; Sato, M.; Untersteller; Xiao, X.-Y. J. Am. Chem. Soc. 1995, 117, 1171-1172.
31. Nicolaou, K. C.; Rutjes, F. P. J. T.; Theodorakis, E. A.; Tiebes, J.; Sato, M.; Untersteller J. Am. Chem. Soc. 1995, 117, 1173-1174.
32. Nicolaou, K. C.; Yang, Z.; Shi, G. Q.; Gunzner, J. L.; Agrios, K. A.; Gartner, P. Nature 1998, 392, 264-269.