Stereoselective synthesis of dihydropyran-4-ones via a formal hetero diels-alder reaction and ceric ammonium nitrate dehydrogenation

Journal of Organic Chemistry

Volumn 61, Issue 21, 1996, Pages 7600-7602

  Evans, P Andrew ^a   Nelson, Jade D ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002648476     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961325u     Document Type: Article

References (45)

1. (a) Doblem, M. Ionophores and Their Structures; Wiley-Interscience: New York, 1981.
2. (b) Westley, J. W., Ed. Polyether Antibiotics; Marcel Dekker: New York, 1982; Vols. I and II.
3. (c) Boivin, T. L. B. Tetrahedron 1987, 43, 3309.
4. (d) Alvarez, E.; Candenas, M. -L.; Perez, R.; Ravelo, J. L.; Martin, J. D. Chem. Rev. 1995, 95, 1953.
5. For recent reviews on the glycosides, see: (a) Danishefsky, S.; DeNinno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15. (b) Postema, M. H. D. Tetrahedron 1992, 48, 8545. (c) Ager, D. J.; East, M. B. Tetrahedron 1993, 49, 5683.
6. For recent reviews on the glycosides, see: (a) Danishefsky, S.; DeNinno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15. (b) Postema, M. H. D. Tetrahedron 1992, 48, 8545. (c) Ager, D. J.; East, M. B. Tetrahedron 1993, 49, 5683.
7. For recent reviews on the glycosides, see: (a) Danishefsky, S.; DeNinno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15. (b) Postema, M. H. D. Tetrahedron 1992, 48, 8545. (c) Ager, D. J.; East, M. B. Tetrahedron 1993, 49, 5683.
8. (a) Paterson, I.; Osborne, S. Tetrahedron Lett. 1990, 31, 2213.
9. (b) Obrecht, D. Helv. Chim. Acta 1991, 74, 27.
10. (c) Coleman, R. S.; Fraser, J. R. J. Org. Chem. 1993, 58, 385.
11. (d) Nangia, A.; Rao, P.-B. Tetrahedron Lett. 1993, 34, 2681 and pertinent references cited therein.
12. Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, CA, 1987.
13. For reviews on the hetero Diels-Alder reaction, see: (a) Danishefsky, S. Aldrichim. Acta 1986, 19, 59. (b) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250. (c) Danishefsky, S. J. Chemtracts 1989, 273. (d) Bednarski, M. D.; Lyssikatos, J. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, p 661.
14. For reviews on the hetero Diels-Alder reaction, see: (a) Danishefsky, S. Aldrichim. Acta 1986, 19, 59. (b) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250. (c) Danishefsky, S. J. Chemtracts 1989, 273. (d) Bednarski, M. D.; Lyssikatos, J. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, p 661.
15. For reviews on the hetero Diels-Alder reaction, see: (a) Danishefsky, S. Aldrichim. Acta 1986, 19, 59. (b) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250. (c) Danishefsky, S. J. Chemtracts 1989, 273. (d) Bednarski, M. D.; Lyssikatos, J. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, p 661.
16. For reviews on the hetero Diels-Alder reaction, see: (a) Danishefsky, S. Aldrichim. Acta 1986, 19, 59. (b) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250. (c) Danishefsky, S. J. Chemtracts 1989, 273. (d) Bednarski, M. D.; Lyssikatos, J. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, p 661.
17. (a) Danishefsky, S. J.; Larson, E.; Askin, D.; Kato, N. J. Am. Chem. Soc. 1985, 107, 1246.
18. (b) Danishefsky, S.; Chao, K.-H.; Schulte, G. J. Org. Chem. 1985, 50, 4650.
19. (c) Danishefsky, S. J.; Maring, C. J. J. Am. Chem. Soc. 1985, 107, 1269.
20. (d) Danishefsky, S. J.; Myles, D. C.; Harvey, D. F. J. Am. Chem. Soc. 1987, 109, 862.
21. (e) Danishefsky, S. J.; DeNinno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082 and pertinent references cited therein.
22. (a) Gould, S. J.; Eisenburg, R. L.; Hillis, L. R. Tetrahedron 1991, 47, 7209.
23. (b) Annunziata, R.; Cinquini, M.; Cozzi, F.; Cozzi, P. G.; Raimondi, L. J. Org. Chem. 1992, 57, 3605.
24. (c) Reetz, M. T.; Gansäuer, G. Tetrahedron 1993, 49, 6025.
25. (d) Yang, G.; Myles, D. C. Tetrahedron Lett. 1994, 35, 2503.
26. (e) Burger, M. T.; Still, W. C. J. Org. Chem. 1996, 61, 775 and pertinent references cited therein.
27. (a) Bednarski, M.; Maring, C.; Danishefsky, S. Tetrahedron Lett. 1983, 24, 3451.
28. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310.
29. (c) Gao, Q.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951.
30. (d) Corey, E. J.; Cywin, C. L. Roper, T. D. Tetrahedron Lett. 1992, 33, 6907.
31. (e) Gao, Q.; Ishihara, K.; Maruyama, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979.
32. (f) Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H. Synlett 1995, 975.
33. (g) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998 and pertinent references cited therein.
34. Evans, P. A.; Longmire, J. M.; Modi, D. P. Tetrahedron Lett. 1995, 36, 3985.
35. For examples of monoactivated dienes in the hetero Diels-Alder reaction, see: (a) Danishefsky, S. J.; Pearson, W. H. J. Org. Chem. 1983, 48, 3865. (b) Danishefsky, S.; Harvey, D. F.; Quallich, G.; Uang, B.-J. J. Org. Chem. 1984, 49, 392. (c) Danishefsky, S. J.; Pearson, W. H.; Harvey, D. F.; Maring, C. J.; Springer, J. P. J. Am. Chem. Soc. 1985, 107, 1256. (d) Danishefsky, S. J.; Uang, B.-J.; Quallich, G. J. Am. Chem. Soc. 1985, 107, 1285. (e) Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. Tetrahedron 1996, 52, 2167 and pertinent references cited therein.
36. For examples of monoactivated dienes in the hetero Diels-Alder reaction, see: (a) Danishefsky, S. J.; Pearson, W. H. J. Org. Chem. 1983, 48, 3865. (b) Danishefsky, S.; Harvey, D. F.; Quallich, G.; Uang, B.-J. J. Org. Chem. 1984, 49, 392. (c) Danishefsky, S. J.; Pearson, W. H.; Harvey, D. F.; Maring, C. J.; Springer, J. P. J. Am. Chem. Soc. 1985, 107, 1256. (d) Danishefsky, S. J.; Uang, B.-J.; Quallich, G. J. Am. Chem. Soc. 1985, 107, 1285. (e) Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. Tetrahedron 1996, 52, 2167 and pertinent references cited therein.
37. For examples of monoactivated dienes in the hetero Diels-Alder reaction, see: (a) Danishefsky, S. J.; Pearson, W. H. J. Org. Chem. 1983, 48, 3865. (b) Danishefsky, S.; Harvey, D. F.; Quallich, G.; Uang, B.-J. J. Org. Chem. 1984, 49, 392. (c) Danishefsky, S. J.; Pearson, W. H.; Harvey, D. F.; Maring, C. J.; Springer, J. P. J. Am. Chem. Soc. 1985, 107, 1256. (d) Danishefsky, S. J.; Uang, B.-J.; Quallich, G. J. Am. Chem. Soc. 1985, 107, 1285. (e) Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. Tetrahedron 1996, 52, 2167 and pertinent references cited therein.
38. For examples of monoactivated dienes in the hetero Diels-Alder reaction, see: (a) Danishefsky, S. J.; Pearson, W. H. J. Org. Chem. 1983, 48, 3865. (b) Danishefsky, S.; Harvey, D. F.; Quallich, G.; Uang, B.-J. J. Org. Chem. 1984, 49, 392. (c) Danishefsky, S. J.; Pearson, W. H.; Harvey, D. F.; Maring, C. J.; Springer, J. P. J. Am. Chem. Soc. 1985, 107, 1256. (d) Danishefsky, S. J.; Uang, B.-J.; Quallich, G. J. Am. Chem. Soc. 1985, 107, 1285. (e) Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. Tetrahedron 1996, 52, 2167 and pertinent references cited therein.
39. For examples of monoactivated dienes in the hetero Diels-Alder reaction, see: (a) Danishefsky, S. J.; Pearson, W. H. J. Org. Chem. 1983, 48, 3865. (b) Danishefsky, S.; Harvey, D. F.; Quallich, G.; Uang, B.-J. J. Org. Chem. 1984, 49, 392. (c) Danishefsky, S. J.; Pearson, W. H.; Harvey, D. F.; Maring, C. J.; Springer, J. P. J. Am. Chem. Soc. 1985, 107, 1256. (d) Danishefsky, S. J.; Uang, B.-J.; Quallich, G. J. Am. Chem. Soc. 1985, 107, 1285. (e) Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. Tetrahedron 1996, 52, 2167 and pertinent references cited therein.
40. The (triisopropylsilyl)oxy diene 1 can be stored at -20 °C for months without decomposition.
41. For a review on the triisopropylsilyl enol ethers, see: Rücker, C. Chem. Rev. 1995, 95, 1009.
42. (a) Magnus, P.; Roe, M. B.; Hulme, C. J. Chem. Soc., Chem. Commun. 1995, 263.
43. (b) Magnus, P.; Lacour, J.; Evans, P. A.; Roe, M. B.; Hulme, C. J. Am. Chem. Soc. 1996, 118, 3406 and pertinent references cited therein.
44. (a) Evans, P. A.; Longmire, J. M. Tetrahedron Lett. 1994, 35, 8345.
45. (b) Evans, P. A.; Modi, D. P. J. Org. Chem. 1995, 60, 6662.