Iron(II)-promoted rearrangement of 1,4-diaryl-2,3-dioxabicyclo[2.2.2]oct-5-enes: A mechanism distinct from that postulated previously

Tetrahedron Letters

Volumn 43, Issue 46, 2002, Pages 8313-8317

  Kamata, Masaki ^a   Satoh, Chika ^a   Kim, Hye Sook ^b   Wataya, Yusuke ^b  

^a NIIGATA UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY   (Japan)

Author keywords

1,4 diaryl 2,3 dioxabicyclo 2.2.2 oct 5 ene; Antimalarial cyclic peroxide; Bicyclic peroxide; Diepoxide; Epoxyketone; FeBr2; Malaria; Mechanism; Rearrangement

Indexed keywords

ALKENE DERIVATIVE; CYCLOHEXANE DERIVATIVE; CYCLOHEXANONE DERIVATIVE; CYCLOPENTANE DERIVATIVE; IRON;

ANTIMALARIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; DRUG DEGRADATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0037064483     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02024-5     Document Type: Article

References (24)

1. Meshnick S.R., Jefford C.W., Posner G.H., Avery M.A., Peters W. Parasitol. Today. 12:1996;79. and references cited therein.
2. McCullough K.J., Nojima M. Curr. Org. Chem. 5:2001;601.
3. Posner G.H., Wang D., Gonzares L., Tao X., Cumming J.N., Klinedinst D., Shapiro T.A. Tetrahedron Lett. 37:1996;815.
4. Posner G.H., Gonzares L., Cumming J.N., Klinedinst D., Shapiro T.A. Tetrahedron. 53:1997;37.
5. Posner G.H., Tao X., Cumming J.N., Klinedinst D., Shapiro T.A. Tetrahedron Lett. 37:1996;7225.
6. Bloodworth A.J., Hagen T., Johnson K.A., Lenoir I., Moussy C. Tetrahedron Lett. 38:1997;635.
7. O'Neil P.M., Bishop L.P., Searle N.L., Maggs J.L., Ward S.A., Bray P.G., Storr R.C., Park B.K. Tetrahedron Lett. 38:1997;4263.
8. Takaya Y., Kurumada K., Takeuji Y., Kim H.-S., Shibata Y., Ikemoto N., Wataya Y., Ohshima Y. Tetrahedron Lett. 39:1997;1361.
9. Kim H.-S., Shibata Y., Wataya Y., Tsuchiya K., Masuyama A., Nojima M. J. Med. Chem. 42:1999;2604.
10. Kim H.-S., Nagai Y., Ono K., Begum K., Wataya Y., Hamada Y., Tsuchiya K., Masuyama A., Nojima M., McCullough K.J. J. Med. Chem. 44:2001;2357.
11. Hindley S.H., Ward S.A., Storr R.C., Searle N.L., Bray P.G., Park B.K., Davies J., O'Neill P.M. J. Med. Chem. 45:2002;1052.
12. Hamada Y., Tokuhara H., Masuyama A., Nojima M., Kim H.-S., Ono K., Ogura N., Wataya Y. J. Med. Chem. 45:2002;1374. and references cited therein.
13. Suzuki M., Ohtake H., Kameya Y., Hamanaka N., Noyori R. J. Org. Chem. 54:1989;5292.
14. Turner J.A., Herz W. J. Org. Chem. 42:1977;1895.
15. Kamata M., Kudoh T., Kaneko J., Kim H.-S., Wataya Y. Tetrahedron Lett. 43:2002;617.
16. Kamata M., Ohta M., Komatsu K., Kim H.-S., Wataya Y. Tetrahedron Lett. 44:2002;2063.
17. Takahashi Y., Wakamatsu K., Morishima S., Miyashi T. J. Chem. Soc., Perkin Trans. 2. 1993;243.
18. Rigaudy J. Horspool W.M., Song P.-S., CRC Handbook of Organic Photochemistry and Photobiology. 1995;325-334 CRC Press, Boca Raton, FL.
19. Posner G.H., Cumming J.N., Ploypradith P., Oh C.H. J. Am. Chem. Soc. 117:1995;5885.
20. Posner G.H., Park S.B., Gonzalez L., Wang D., Cumming J.N., Klinedinst D., Shapiro T.A., Bachi M.D. J. Am. Chem. Soc. 118:1996;3537.
21. Cumming J.N., Wang D., Park S.B., Shapiro T.A., Posner G.H. J. Med. Chem. 41:1998;952.
22. Traylor T.G., Miksztsal A.R. J. Am. Chem. Soc. 109:1987;2770.
23. Abe M., Inakazu T., Munakata J., Nojima M. J. Am. Chem. Soc. 121:1999;6556. and references cited therein.
24. Iranpoor N., Salehi P. Synthesis. 1994;1152.