Resolution of (±)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol via Candida cylindracea lipase: Synthesis of (-)- and (+)-proto-quercitol

Tetrahedron Asymmetry

Volumn 15, Issue 3, 2004, Pages 453-456

  Gültekin, M Serdar ^a,b   Çelik, Murat ^a,b   Turkut, Engin ^a   Tanyeli, Cihangir ^a   Balci, Metin ^a  

^a MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

^b ATATÜRK UNIVERSITY   (Turkey)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ALCOHOL; ENDOPEROXIDE; FUNGAL ENZYME; HYDROPEROXIDE DERIVATIVE; INOSITOL DERIVATIVE; QUERCITOL; THIOUREA; TITANIUM DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CANDIDA; CANDIDA CYLINDRACEA; CHEMICAL BOND; COMPLEX FORMATION; CONTROLLED STUDY; DRUG SYNTHESIS; ENANTIOSELECTIVITY; NONHUMAN; OXIDATION; PHOTOOXIDATION; PRIORITY JOURNAL; REDUCTION KINETICS;

EID: 0742306896     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.11.037     Document Type: Article

References (31)

1. Posternak T. The Cyclitols. 1965;Hermann, Paris.
2. Hudlicky T., Cebulak M. Cyclitols and Their Derivative. 1993;VCH, Weinheim.
3. Billington D.C. The Inositol Phosphates. 1993;VCH, Weinheim.
4. Berridge M.J. Nature. 361:1993;315-325.
5. Balci M., Sütbeyaz Y., Secen H. Tetrahedron. 46:1990;3715-3742.
6. Podeschwa M., Plettenburg O., vom Brocke J., Block O., Adelt S., Altenbach H.-J. Eur. J. Org. Chem. 2003;1958-1971.
7. Gibson D.T., Zylstra G.J. J. Biol. Chem. 7:1989;2653.
8. Gibson D.T., Hensley M., Yoshida H., Mabry R. Biochemistry. 9:1970;1626.
9. Gibson D.T., Mahaderan V., Davey J.R. Bacteriol. 119:1974;1626.
10. Carless H.A.J. Tetrahedron: Asymmetry. 3:1992;795-826.
11. Stinson S.C. Chem. Eng. News. September 28:1992;46.
12. Sheldon R.A. Chirotechnology. 1993;Marcel Decker, New York.
13. Collins A.N., Sheldrake G.N. Crosby J. Chirality in Industry. Vol. I:1992;Wiley, Chichester. 1997; Vol. II.
14. Stinson S.C. Chem. Eng. News. 28:1998;46.
15. Faber K. Biotransformations in Organic Chemistry. 3rd ed. 1997;Springer, Heidelberg.
16. Ladner W.E., Whitesides G.M. J. Am. Chem. Soc. 106:1984;7250.
17. Zaks A., Klibanov A.M. Science. 224:1984;1249.
18. Zaks A., Klibanov A.M. Proc. Natl. Acad. Sci. U.S.A. 82:1985;3192.
19. Sweers H.M., Wong C.-H. J. Am. Chem. Soc. 108:1986;6421.
20. Wang Y.-F., Wong C.-H. J. Org. Chem. 53:1988;3127.
21. Adam W., Balci M., Kilic H. J. Org. Chem. 65:2000;5926-5931.
22. Posternak T. Helv. Chim. Acta. 15:1932;948.
23. McCasland G.E., Naumann M.O., Durham L.J. J. Org. Chem. 33:1968;4220.
24. Secen H., Salamci E., Sutbeyaz Y., Balci M. Synlett. 1993;609-610.
25. Salamci E., Secen H., Sutbeyaz Y., Balci M. J. Org. Chem. 62:1997;2453-2457.
26. For the synthesis of protected isomeric cyclohexenetriols see: de Sousa S.E., O'Brien P., Pilgram C.D. Tetrahedron. 58:2002;4643-4654.
27. Kee A., O'Brien P., Pilgram C.D., Watson S.T. Chem. Commun. 2000;1521-1522.
28. Maezaki N., Nagahashi N., Yoshigami R., Iwata C., Tanaka T. Tetrahedron Lett. 40:1999;3781-3784.
29. Haines A.H., King A.S.H., Knight J.R., Nguyen V.-A. Tetrahedron Lett. 39:1998;4393-4396.
30. Kim K.S., Park J.I., Moon H.K., Yi H. Chem. Commun. 1998;1945-1946.
31. Gultekin M.S., Salamci E., Balci E. Carbohydr. Res. 338:2003;1615.