Stereoselective ring-opening reactions with AcBr and AcCl. A new method for preparation of some haloconduritols

Tetrahedron

Volumn 60, Issue 4, 2004, Pages 861-866

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

^a ATATÜRK UNIVERSITY   (Turkey)

Author keywords

7 Oxa bicyclo 2.2.1 hept 5 ene 2,3 diol diacetate; Acetyl bromide; Acetyl chloride; Cyclohexa 3,5 diene cis 1,2 diol; Haloconduritol; Ring opening

Indexed keywords

(1ALPHA,2ALPHA,3ALPHA,6BETA) 6 CHLORO 4 CYCLOHEXENE 1,2,3 TRIOL; (1ALPHA,2ALPHA,3ALPHA,6BETA) 6 CHLORO 4 CYCLOHEXENE 1,2,3 TRIOL TRIACETATE; (3AALPHA,5ABETA,6ABETA,6BALPHA) 2,2 DIMETHYL 3A,5A,6A,6B TETRAHYDROOXIRENO[E] 1,3 BENZODIOXOLE; 5,6 DIBROMO 7 OXABICYCLO[2.2.1]HEPTAN 2,3 DIOL DIACETATE; 7 OXABICYCLO[2.2.1]HEPT 5 ENE 2,3 DIOL DIACETATE; 7 OXABICYCLO[2.2.1]HEPTANE 2,3 DIOL DIACETATE; ACETOACETIC ACID DERIVATIVE; ALKADIENE; BROMINE DERIVATIVE; CHLORINE DERIVATIVE; CYCLOHEXA 3,5 DIENE 1,2 DIOL; GLYCOSIDASE INHIBITOR; HYDROCHLORIC ACID; SULFURIC ACID; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; METHODOLOGY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; STEREOCHEMISTRY; TRANSESTERIFICATION;

EID: 0346339686     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.11.054     Document Type: Article

References (31)

1. Tatsuta K. Chapleur Y. Carbohydrate mimics: concepts and methods. 1998;283-305 Wiley-VCH, Weinheim.
2. Elbein A.D. Methods Enzymol. 138:1987;661-709. (Complex Carbohydr., Pt. E).
3. Elbein A.D. Annu. Rev. Biochem. 56:1987;497-534.
4. Elbein A.D. FASEB J. 5:1991;3055-3063.
5. Legler G. Methods Enzymol. 46:1977;368-381.
6. Salvucci M.E. Arch. Insect Biochem. 45:2000;117-128.
7. Trudel G.C., Herscovics A., Holland P.C. Biochem. Cell Biol. 66:1988;1119-1125.
8. Alonso J.M., Santa-Cecilia A., Calvo P. Eur. J. Biochem. 215:1993;37-42.
9. Guo Z.X., Haines A.H., Taylor R.J.K. Synlett. 1993;607-608.
10. Guo Z.X., Haines A.H., Pyke S.M., Pyke S.G., Taylor R.J.K. Carbohydr. Res. 264:1994;147-153.
11. Haines A.H., King A.S.H., Knight J.R., Nguyen V.A. Tetrahedron Lett. 39:1998;4393-4396.
12. Hudlicky T., Luna H., Olivo H.F., Andersen C., Nugent T., Price J.D. J. Chem. Soc. Perkin Trans. 1. 1991;2907-2917.
13. Baran A., Kazaz C., Seçen H., Sütbeyaz Y. Tetrahedron. 59:2003;3643-3648.
14. Mikhailov B.M., Nikolaeva N.D. Izv. Akad. Nauk. SSSR, Ser. Khim. 1963;1368-1373. Chem. Abstr. 1963, 59, 15296.
15. 20114 Polivka Z., Feries M. Chem. Abstr. 70:1969;869-894.
16. Smorgonskii L.M. Zh. Obshch. Khim. 17:1947;416-420.
17. Iqbal J., Khan M.A., Srivastava R.R. Tetrahedron Lett. 29:1988;4985-4986.
18. Iqbal J., Srivastava R.R. Tetrahedron. 47:1991;3155-3170.
19. Bhar S., Ranu B.C. J. Org. Chem. 60:1995;745-747.
20. Jung P.M.J., Motherwell W.B., Williams A.S. Chem. Commun. 1997;1283-1284. We thank Professor W. B. Motherwell for providing unpublished NMR data of (1α,2α,3α,6β)-6-bromo-4-cyclohexene-1,2,3-triol triacetate.
21. Dastan A., Demir U., Balci M. J. Org. Chem. 59:1994;6534-6538.
22. Senocak E., Taskesenligil Y., Tumer F. Turk. J. Chem. 26:2002;939-945.
23. Carless H.A.J. Tetrahedron Lett. 33:1992;6379-6382.
24. Ramesh K., Wolfe M.S., Lee Y., Velde D.V., Borchardt R.T. J. Org. Chem. 57:1992;5861-5868.
25. Seçen H., Gültekin S., Sütbeyaz Y., Balci M. Synth. Commun. 24:1994;2103-2108.
26. Hudlicky T., Thorpe A.J. Synlett. 1994;899-901.
27. Hudlicky T., Abboud K.A., Entwistle D.A., Fan R., Maurya R., Thorpe A.J., Bolonick J., Myers B. Synthesis. 1996;897-911.
28. Banwell M.G., Haddad N., Hudlicky T., Nugent T.C., Mackay M.F., Richards S.L. J. Chem. Soc., Perkin Trans. 1. 1997;1779-1791.
29. Jarvest R.L., Berge J.M., Houge-Frydrych C.S.V., Mensah L.M., O'Hanlon P.J., Pope A.J. Bioorg. Med. Chem. Lett. 2001;2499-2502.
30. Hudlicky T., Tian X., Königsberger K., Rouden J. J. Org. Chem. 59:1994;4037-4039.
31. Yang N.C., Chen M.J., Chen P. J. Am. Chem. Soc. 106:1984;7310-7315.