Synthesis of haloconduritols from an endo-cycloadduct of furan and vinylene carbonate

Tetrahedron

Volumn 59, Issue 20, 2003, Pages 3643-3648

  Baran, Arif ^a   Kazaz, Cavit ^a   Seçen, Hasan ^a   Sütbeyaz, Yaşar ^a  

^a ATATÜRK UNIVERSITY   (Turkey)

Author keywords

Boron trihalides; Cycloaddition; Furan; Haloconduritol; Neighboring group participation; Ring opening; Trans esterification; Vinylene carbonate

Indexed keywords

(1ALPHA,2ALPHA,3BETA,6BETA) 6 HALOGENO 4 CYCLOHEXENE 1,2,3 TRIOL; (1ALPHA,2ALPHA,3BETA,6BETA) 6 HALOGENO 4 CYCLOHEXENE 1,2,3 TRIOL 1,2 DIACETATE; ACETOACETIC ACID; ACETOACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; BORON TRIHALIDE; CARBONIC ACID DERIVATIVE; FURAN; FURAN DERIVATIVE; HALIDE; PYRIDINE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYLENE CARBONATE;

ACETYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLOADDITION; DIELS ALDER REACTION; ESTERIFICATION; HYDROLYSIS; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

BETULACEAE;

EID: 0038065306     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00510-6     Document Type: Article

References (32)

1. (a) Elbein A.D. Methods Enzymol. 138:1987;661-709.
2. (b) Elbein A.D. Annu. Rev. Biochem. 56:1987;497-534
3. (c) Elbein A.D. FASEB J. 5:1991;3055-3063
4. (d) Legler G. Methods Enzymol. 46:1977;368-381
5. (e) Salvucci M.E. Arch. Insect Biochem. 45:2000;117-128
6. (f) Trudel G.C., Herscovics A., Holland P.C. Biochem. Cell. Biol. 66:1988;1119-1125
7. (g) Alonso J.M., Santa-Cecilia A., Calvo P. Eur. J. Biochem. 215:1993;37-42.
8. Guo Z.X., Haines A.H., Taylor R.J.K. Synlett. 1993;607-608.
9. Guo Z.X., Haines A.H., Pyke S.M., Pyke S.G., Taylor R.J.K. Carbohydr. Res. 264:1994;147-153.
10. Haines A.H., King A.S.H., Knight J.R., Nguyen V.A. Tetrahedron Lett. 39:1998;4393-4396.
11. Hudlicky T., Luna H., Olivo H.F., Andersen C., Nugent T., Price J.D. J. Chem. Soc., Perkin Trans. 1. 1991;2907-2917.
12. Yur'ev Y.K., Zefirov N.S. Zhur. Obshchei Khim. 31:1961;685-686.
13. (a) Youssefyeh R.D., Mazur Y. Chem. Ind. (London). 1963;609-610
14. (b) Stehle V., Brini M., Pousse A. Bull. Soc.Chim. Fr. 1969;2171-2175
15. (c) Cabiddu S., Maccioni A., Mura L., Secci M. Rend. Semin. Fac. Sci. Univ. Cagliari. 45:1975;113-116.
16. (c) Cabiddu S., Maccioni A., Mura L., Secci M. Rend. Semin. Fac. Sci. Univ. Cagliari. 45:1975;113-116. Chem. Abstr., 1976, 84; 164216
17. (d) Coe, J.; Wirtz, M. C.; Brooks, P. R.; Rescek, D. M.; Woodworth, G. F.; Morgan, B. P. Book of Abstracts, 219th ACS National Meeting, San Francisco, CA, March 26-30, 2000; American Chemical Society: Washington, DC; ORGN-579.
18. (e) Bhatt M.V., Kulkarni S.U. Synthesis. 1983;249-282.
19. Jotterand N., Vogel P., Schenk K. Helv. Chim. Acta. 82:1999;821-847.
20. Newman M.S., Addor R.W. J. Am. Chem. Soc. 77:1955;3789-3793.
21. Le Drian C., Vieira E., Vogel P. Helv. Chim. Acta. 72:1989;338-347.
22. Jung P.M.J., Motherwell W.B., Williams A.S. Chem. Commun. 1997;1283-1284.
23. Kohrt J.T., Gu J.X., Johnson J.R. J. Org. Chem. 63:1998;5088-5093. and see the supporting material of the publication on the web.
24. We thank Professor Dr A. H. Haines for providing unpublished data on these compounds.
25. Allemann S., Vogel P. Helv. Chim. Acta. 77:1994;1-9.
26. (a) Balci M., Sutbeyaz Y., Secen H. Tetrahedron. 46:1990;3715-3742
27. (b) Secen H., Sutbeyaz Y., Balci M. Tetrahedron Lett. 31:1990;1323-1326.
28. Sutbeyaz Y., Secen H., Balci M. J. Chem. Soc., Chem. Commun. 1988;1330-1331.
29. (a) Hartman J.S., Miller J.M. Inorg. Nucl. Chem. Lett. 5:1969;831-835
30. (b) Bula M.J., Hamilton D.E., Hartman J.S. J. Chem. Soc., Dalton Trans. 1972;1405-1412.
31. Kowarski C.R., Sarel S. J. Org. Chem. 38:1973;117-119.
32. Bazan C.B., Oskam J.H., Cho H.N., Park L.Y., Schrock R.R. J. Am. Chem. Soc. 113:1991;6899-6907.