Synthesis of new type diacetal trioxa-cage compounds via an intramolecular nucleophilic addition of the hydroxy group to the carbonyl oxide group

Journal of Organic Chemistry

Volumn 63, Issue 22, 1998, Pages 7687-7693

  Wu Hsien Jen, ^a   Chao, Ching Shiun ^a   Lin Chu Chung, ^a  

^a NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000914723     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980632s     Document Type: Article

References (62)

1. For review, see: (a) Eaton, P. EAngew. Chem., Int. Ed. Engl. 1992, 31, 1421.
2. (b) Griffin, G. W.; Marchand, A. P. Chem. Rev. 1989, 89, 997.
3. (c) Marchand, A. P. Chem. Rev. 1989, 89, 1011.
4. (d) Paquette, L. A. Chem. Rev. 1989, 89, 1051.
5. (e) Klunder, A. J. H.; Zwanenburg, B. Chem. Reu. 1989,89, 1035.
6. (£) Osawa, E.; Yonemitsu, O. Carbocylic Cage Compounds; VCH: New York, 1992.
7. (g) Olah, G. A. Cage Hydrocarbons; J. Wiley & Sons, Inc.: New York, 1990.
8. (a) Mehta, G.; Nair, M. S. J. Chem. Soc., Chem. Commun. 1983, 439.
9. (b) Shen, K. W. J. Am. Chem. Soc. 1971, 93, 3064.
10. (c) Allred, E. L.; Beck, B. R. Tetrahedron Lett. 1974,437.
11. (d) Barborak, J. C.; Khoury, D.; Maier, W. F.; Schleyer, P. V. R.; Smith, E. C.; Smith, Jr. W. F.; Wyrick, C. J. Org. Chem. 1974, 44, 4761.
12. (a) Prinzbach, H.; Klaus, M. Angew. Chem., Int. Ed. Engl. 1969, 8, 276.
13. (b) Marchand, A. P.; Reddy, G. M.; Watson, W. H.; Kashyap, R. Tetrahedron 1990, 46, 3409.
14. (a) Sasaki, T.; Eguchi, S.; Kiriyama, T.; Hiroaki, O. Tetrahedron 1974,30, 2707.
15. (b) Singh, P. J. Org. Chem. 1979,44, 843.
16. (c) Coxon, J. M.; Fong, S. T.; McDonald, D. Q.; O'Connell, M. J.; Steel, P. J. Tetrahedron Lett. 1991, 32, 7115.
17. Suri, S. C. J. Org. Chem. 1993, 58, 4153.
18. (a) Mehta, G.; Srikrishna, A.; Reddy, A. V.; Nair, M. S. Tetrahedron 1981, 37, 4543.
19. (b) Mehta, G.; Nair, M. S. J. Am. Chem. Soc. 1985,107, 7519.
20. (c) Marchand, A. P.; LaRoe, W. D.; Sharma, G. M.; Suri, S. C.; Reddy, D. S. J. Org. Chem. 1986,51,1622.
21. (d) Fessner, W. D.; Prinzbach, H. Tetrahedron 1986, 42, 1797.
22. (e) Smith, E. C.; Barborak, J. C. J. Org. Chem. 1976, 41, 1433.
23. (a) Marchand, A. P.; Chou, T. C. Tetrahedron 1975, 31, 2655.
24. (b) Mehta, G.; Reddy, K R. J. Org. Chem. 1987, 52, 460.
25. (a) Mehta, G.; Rao, H. S. P. J. Chem. Soc., Chem. Commun. 1986, 472.
26. (b) Mehta, G.; Rao, H. S. P.; Reddy, K. R. J. Chem. Sac., Chem. Commun. 1987, 78.
27. (a) Wu, G. Y.; Lin, C. C.; Lai, M. C.; Wu, H. J. J. Chin. Chem. Soc. 1996, 43, 187.
28. (b) Wu, H.. J.; Wu, C. Y.; Lin, C. C. Chin. Chem. Lett. 1996, 7, 15.
29. (a) Wu, H. J.; Lin, C. C. J. Org. Chem. 1995, 60, 7558.
30. (b) Wu, H. J.; Lin, C. C. J. Org. Chem. 1996,61,3820.
31. (c) Wu, H. J.; Chern, J. H.; Wu, C. Y. Tetrahedron 1997,53, 2401.
32. (d) Wu, H. J.; Chern, J. H. Tetrahedron 1997, 53, 17653.
33. (e) Lin, C. C.; Wu, H. J. Tetrahedron Lett. 1995, 36, 9353.
34. (0 Wu, H. J.; Huang, F. J.; Lin, C. C. J. Chem. Soc., Chem. Commun. 1991, 770.
35. (g) Lin, C. C.; Wu, H. J. J. Chin. Chem. Soc. 1995,42, 815.
36. (h) Lin, C. C.; Huang, F. J.; Lin, J. C.; Wu, H. J. J. Chin. Chem. Soc. 1996,43,177.
37. Lin, R. L.; Wu, C. Y.; Chern, J. H.; Wu, H. J. J. Chin. Chem. Soc. 1996, 43, 289. j)
38. Chern, J. H.; Wu, H. J. J. Chin. Chem. Soc. 1998, in press.
39. Lin, C. C.; Wu, H. J. Synthesis 1996, 715.
40. (a) Wu, H. J.; Wu, C. Y. Tetrahedron Lett. 1997, 38, 2493.
41. (b) Mehta, G.; Vidya, R. Tetrahedron Lett. 1997, 38, 4173.
42. (a) Wu, H. J.; Chern, J. H. J. Org. Chem. 1997, 62, 3208.
43. (b) Wu, H. J.; Chern, J. H. J. Chem. Soc., Chem. Commun. 1997,547.
44. (c) Wu, H. J.; Chern, J. H. Tetrahedron Lett. 1997,38, 2887.
45. (d) Chern, J. H.; Wu, H. J. J. Chin. Chem. Soc. 1997, 44, 71.
46. (e) Chern, J. H.; Wu. H. J. Tetrahedron 1998, 54, 5967.
47. (a) Wu, H. J.; Tsai, S. H.; Chern, J. H.; Lin, H. C. J. Org. Chem. 1997, 62, 6367.
48. (b) Wu, H. J.; Tsai, S. H.; Chung, W. S. Tetrahedron Lett. 1996,37, 8209.
49. (e) Wu, H. J.; Tsai, S. H.; Chung, W. S. J. Chem. Soc., Chem. Commun. 1996, 375.
50. (d) Tsai, S. H.; Wu, H. J.; Chung, W. S. J. Chin. Chem. Soc. 1996, 43, 445.
51. (a) Bailey, P. S. Ozonation in Organic Chemistry; Academic Press: New York, 1978; Vol. 1;
52. 1982; Vol. 2.
53. (b) Bunnelle, W. H. Chem. Rev. 1991, 91, 335.
54. (c) McCullough, K. J.; Nojima, M. In Organic Peroxides; Ando, W., Ed.; Wiley: New York, 1992.
55. (d) Sander, W. Angew. Chem., Int. Ed. Engl. 1990, 29, 344.
56. (a) Griesbaum, K.; Kiesel, G. Chem. Ber. 1989, 722, 145.
57. (b) Paryzek, Z.; Martynow, J.; Swoboda, W. J. Chem. Soc., Perkin Trans. 1 1990,1222.
58. (c) Bunnelle, W. H.; Isbell, T. A. J. Org. Chem. 1992,57, 729.
59. Teshima, K.; Kawamura, S. I.; Ushigoe, Y.; Nojima, M.; McCullough, K. J. J. Org. Chem. 1995, 60, 4755.
60. (a) Schreiber, S. L.; Claus, R. E.; Geagan, J. Tetrahedron Lett. 1982, 23, 3867.
61. (b) Hon, Y. S.; Yan, J. L. Tetrahedron Lett. 1993, 34, 6591.
62. Lin, H. C.; Wu, C. Y.; Wu, H. J. J. Chin. Chem. Soc. 1997,44, 609.