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

Date

2004-02-09

Author

GÜLTEKİN, M SERDAR
Celik, M
TURKUT, ENGİN
Tanyeli, Cihangir
BALCİ, METİN

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Photooxygenation of cyclohexa-1,4-diene afforded anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-yl hydroperoxide. The hydroperoxy endoperoxide was reduced with dimethylsulfide-titanium tetraisopropoxide to produce ()-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol. The highly efficient enantioselective resolution of the racemic (+/-)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol was accomplished with Candida cylindracea lipase (CCL) to produce the enantiomerically enriched alcohol and the corresponding acetate: The cleavage of the peroxide linkage by thiourea followed by the oxidation of the double bond with OsO4 resulted in the formation of (-)-proto-quercitol and (+)-proto-quercitol, respectively.

Subject Keywords

Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Catalysis

URI

https://hdl.handle.net/11511/48229

Journal

TETRAHEDRON-ASYMMETRY

DOI

https://doi.org/10.1016/j.tetasy.2003.11.037

Collections

Department of Chemistry, Article

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Citation Formats

M. S. GÜLTEKİN, M. Celik, E. TURKUT, C. Tanyeli, and M. BALCİ, “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, pp. 453–456, 2004, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/48229.