New methods for the synthesis of oxy-functionalizefd 1,2,4-trioxanes and 1,2,4-trioxepanes from unsaturated hydroperoxy acetals

Tetrahedron Letters

Volumn 38, Issue 50, 1997, Pages 8753-8756

  Ushigoe, Yoshihiro ^a   Masuyama, Araki ^a   Nojima, Masatomo ^a   McCullough, Kevin J ^b  

^a OSAKA UNIVERSITY   (Japan)

^b HERIOT WATT UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 TRIOXANE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

OXY;

EID: 0030834547     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10343-4     Document Type: Article

References (26)

1. (a) Posner, G. H.; Tao, X.; Cumming, J. N.; Klinedinst, D.; Shapiro, T. A. Tetrahedron Lett. 1996, 37, 7225;
2. (b) Jefford, C. W.; Vicente, M. G. H.; Jacquier, Y.; Favarger, F.; Mareda, J.; Millasson-Schmidt, P.; Brunner, G.; Burger, U. Helv. Chim. Acta 1996, 79, 1475;
3. (c) Haynes, R. K.; Vonwiller, S. C. Acc. Chem. Res. 1997, 30, 73.
4. (a) Bloodworth, A. J.; Hagen, T.; Johnson, K. A.; LeNoir, I.; Moussy, C. Tetrahedron Lett. 1997, 38, 635;
5. (b) Dusssault, P. H.; Zope, U. R. J. Org. Chem. 1995, 60, 8218;
6. (c) Jefford, C. W.; McGoran, E. C.; Boukouvalas, J.; Richardson, G.; Robinson, B. L.; Peters, W. Helv. Chim. Acta 1988, 71, 1805;
7. (d) Bloodworth, A. J.; Johnson, K. A.Tetrahedron Lett., 1994, 35, 8057;
8. (e) Bunnelle, W. H.; Isbell, T. A.; Barnes, C. L.; Quails, S. J. Am. Chem. Soc., 1991, 113, 8168;
9. (f) Zhou, W. -S. Xu, X. -X. Acc. Chem. Res., 1994, 27, 211.
10. Ushigoe, Y.; Kano, Y.; Nojima, M. J. Chem. Soc., Perkin Trans. 1, 1997, 5.
11. See also (a) Dussault, P. H.; Davies, D. R. Tetrahedron Lett., 1996, 37, 463;
12. (b) Dussault, P. H.; Lee, H.-J.; Niu, Q. J. J. Org. Chem. 1995, 60, 784.
13. Ushigoe, Y.; Torao, Y.; Masuyama, A.; Nojima M. J. Org. Chem. in press.
14. (a) Porter, N. A. "Organic Peroxides," Ando, W. Ed.; Wiley, New York, 1992, chapter 2;
15. (b) Porter, N. A.; Funk, M. O.; Gilmore, D.; Isaac, R.; Nixon, J. J. Am. Chem. Soc. 1976, 98, 6000;
16. (c) Dussault, P. H.; Woller, K. J. Am. Chem. Soc. 1997, 119, 3824.
17. (a) Boukouvalas, J.; Pouliot, R.; Fréchette, Y. Tetrahedron Lett. 1995, 36, 4167.
18. (b) Fielder, S.; Rowan, D. D.; Sherburn, M. S. Synlett 1996, 349.
19. 5: C, 56.88; H, 8.68. Found: C, 56.93; H, 8.74.
20. (a) Russell, G. A. J. Am. Chem. Soc. 1957, 79, 3871.
21. (b) Porter, N. A. "Organic Peroxides," Ando, W. Ed.; Wiley, New York, 1992, chapter 2, p. 114.
22. Jefford, C. W.; Jaggi, D.; Boukouvalas, J.; Kohmoto, S. J. Am. Chem. Soc. 1983, 105, 6497.
23. 4: C, 61.09; H, 9.32. Found: C, 60.68; H, 8.77.
24. (a) Jefford, C. W.; Jaber, A.; Boukouvalas, J. Synthesis 1988, 391;
25. (b) Jefford, C. W.; Rossier, J.-C.; Richardson, G. D. J. Chem. Soc., Chem. Commun.. 1983, 1064.
26. 4: C, 62.85; H, 6.84. Found: C, 62.80; H, 6.66.