Synthesis of Tetraacetal Tetraoxa-Cage Compounds with Alkyl Substituents at Different Sites of the Oxa-Cage Skeleton

Journal of the Chinese Chemical Society

Volumn 43, Issue 3, 1996, Pages 289-295

  Lin, Rong Liang ^a   Wu, Chung Yi ^a   Chern, Jyh Haur ^a   Wu, Hsien Jen ^a  

^a NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

Author keywords

Alkyl substituents; Ozonolysis; Synthesis of tetraacetal tetraoxa cages

Indexed keywords

EID: 0000465738     PISSN: 00094536     EISSN: None     Source Type: Journal    
DOI: 10.1002/jccs.199600042     Document Type: Article

References (35)

1. For reviews, see: (a) Eaton, P. E. Angew. Chem. Int. Ed. Engl. 1992, 31, 1421. (b) Griffin, G. W.; Marchand, A. P. Chem. Rev. 1989, 89, 997. (c) Machand, A. P. Chem. Rev. 1989, 89, 1011. (d) Paquette, L. A. Chem. Rev. 1989, 89, 1051. (e) Klunder, A. J. H.; Zwanenburg, B. Chem. Rev. 1989, 89, 1035. (f) Mehta, G.; Marchand, A. P.; Dilling, W. L. In Carbocylic Cage Compounds; Osawa, E.; Yonemitsu, O. Ed.; VCH: New York, 1992.
2. For reviews, see: (a) Eaton, P. E. Angew. Chem. Int. Ed. Engl. 1992, 31, 1421. (b) Griffin, G. W.; Marchand, A. P. Chem. Rev. 1989, 89, 997. (c) Machand, A. P. Chem. Rev. 1989, 89, 1011. (d) Paquette, L. A. Chem. Rev. 1989, 89, 1051. (e) Klunder, A. J. H.; Zwanenburg, B. Chem. Rev. 1989, 89, 1035. (f) Mehta, G.; Marchand, A. P.; Dilling, W. L. In Carbocylic Cage Compounds; Osawa, E.; Yonemitsu, O. Ed.; VCH: New York, 1992.
3. For reviews, see: (a) Eaton, P. E. Angew. Chem. Int. Ed. Engl. 1992, 31, 1421. (b) Griffin, G. W.; Marchand, A. P. Chem. Rev. 1989, 89, 997. (c) Machand, A. P. Chem. Rev. 1989, 89, 1011. (d) Paquette, L. A. Chem. Rev. 1989, 89, 1051. (e) Klunder, A. J. H.; Zwanenburg, B. Chem. Rev. 1989, 89, 1035. (f) Mehta, G.; Marchand, A. P.; Dilling, W. L. In Carbocylic Cage Compounds; Osawa, E.; Yonemitsu, O. Ed.; VCH: New York, 1992.
4. For reviews, see: (a) Eaton, P. E. Angew. Chem. Int. Ed. Engl. 1992, 31, 1421. (b) Griffin, G. W.; Marchand, A. P. Chem. Rev. 1989, 89, 997. (c) Machand, A. P. Chem. Rev. 1989, 89, 1011. (d) Paquette, L. A. Chem. Rev. 1989, 89, 1051. (e) Klunder, A. J. H.; Zwanenburg, B. Chem. Rev. 1989, 89, 1035. (f) Mehta, G.; Marchand, A. P.; Dilling, W. L. In Carbocylic Cage Compounds; Osawa, E.; Yonemitsu, O. Ed.; VCH: New York, 1992.
5. For reviews, see: (a) Eaton, P. E. Angew. Chem. Int. Ed. Engl. 1992, 31, 1421. (b) Griffin, G. W.; Marchand, A. P. Chem. Rev. 1989, 89, 997. (c) Machand, A. P. Chem. Rev. 1989, 89, 1011. (d) Paquette, L. A. Chem. Rev. 1989, 89, 1051. (e) Klunder, A. J. H.; Zwanenburg, B. Chem. Rev. 1989, 89, 1035. (f) Mehta, G.; Marchand, A. P.; Dilling, W. L. In Carbocylic Cage Compounds; Osawa, E.; Yonemitsu, O. Ed.; VCH: New York, 1992.
6. For reviews, see: (a) Eaton, P. E. Angew. Chem. Int. Ed. Engl. 1992, 31, 1421. (b) Griffin, G. W.; Marchand, A. P. Chem. Rev. 1989, 89, 997. (c) Machand, A. P. Chem. Rev. 1989, 89, 1011. (d) Paquette, L. A. Chem. Rev. 1989, 89, 1051. (e) Klunder, A. J. H.; Zwanenburg, B. Chem. Rev. 1989, 89, 1035. (f) Mehta, G.; Marchand, A. P.; Dilling, W. L. In Carbocylic Cage Compounds; Osawa, E.; Yonemitsu, O. Ed.; VCH: New York, 1992.
7. (a) Mehta, G.; Nair, M. S. J. Chem. Soc. Chem. Commun. 1983, 439.
8. (b) Shen, K. W. J. Am. Chem. Soc. 1971, 93, 3064.
9. (c) Allred, E. L.; Beck, B. R. Tetrahedron Lett. 1974, 437.
10. (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. 1979, 44, 4761.
11. (a) Prinzbach, H.; Klaus, M. Angew. Chem., Int. Ed. Engl. 1969, 8, 276.
12. (b) Marchand, A. P.; Reddy, G. M.; Watson, W. H.; Kashyap, R. Tetrahedron 1990, 46, 3409.
13. (a) Sasaki, T.; Eguchi, S.; Kiriyama, T.; Hiroaki, O. Tetrahedron 1974, 30, 2707.
14. (b) Singh, P. J. Org. Chem. 1979, 44, 843.
15. (c) Coxon, J. M.; Fong, S. T.; McDonald, D. Q.; O'Connell, M. J.; Steel, P. J. Tetrahedron Lett. 1991, 32, 7115.
16. Suri, S. C. J. Org. Chem. 1993, 58, 4153.
17. (a) Mehta, G.; Srikrishna, A.; Reddy, A. V.; Nair, M. S. Tetrahedron 1981, 37, 4543.
18. (b) Mehta, G.; Nair, M. S. J. Am. Chem. Soc. 1985, 107, 7519.
19. (c) Marchand, A. P.; LaRoe, W. D.; Sharma, G. V. M.; Suri, S. C.; Reddy, D. S. J. Org. Chem. 1986, 51, 1622.
20. (d) Fessner, W. D.; Prinzbach, H. Tetrahedron 1986, 42, 1797.
21. (e) Smith, E. C.; Barborak, J. C. J. Org. Chem. 1976, 41, 1433.
22. (a) Marchand, A. P.; Chou, T. C. Tetrahedron 1975, 31, 2655.
23. (b) Mehta, G.; Reddy, K. R. J. Org. Chem. 1987, 52, 460.
24. Metha, G.; Rao, H. S. P. J. Chem. Soc. Chem. Commun. 1986, 472.
25. (b) Metha, G.; Rao, H. S. P.; Reddy, K. R. J. Chem. Soc. Chem. Commun. 1987, 78.
26. (a) Wu, H. J.; Huang, F. J.; Lin. C. C. J. Chem. Soc. Chem. Commun. 1991, 770.
27. (b) Lin, C. C.; Huang, F. J.; Lin, J. C.; Wu, H. J. J. Chin. Chem. Soc. 1996 (in press).
28. (a) Wu, H. J.; Lin, C. C. J. Org. Chem. 1995, 60, 7558.
29. (b) Lin, C. C.; Wu, H. J. J. Chin. Chem. Soc. 1995, 42, 815.
30. (c) Lin, C. C.; Wu, H. J. Tetrahedron Lett. 1995, 36, 9353.
31. (d) Lin, C. C.; Wu, H. J. Synthesis 1996 (in press).
32. (a) Alder, K.; Ache, H. J.; Flock, F. Chem. Ber. 1960, 93, 1888.
33. (b) Clark, R. A.; Fiato, R. A. J. Am. Chem. Soc. 1970, 92, 4736.
34. Sternbach, D. D.; Hobbs, S. H. Syn. Commun. 1984, 14, 1305.
35. Quantitative NOE experiments: irradiated δ 0.94 (the proton on the apex carbon of 8), enhanced δ 3.36 (14%, the exo proton of 8, 8% for the two bridgehead protons).