676543-81-0Relevant articles and documents
Resolution of (±)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol via Candida cylindracea lipase: Synthesis of (-)- and (+)-proto-quercitol
Gueltekin, M. Serdar,Celik, Murat,Turkut, Engin,Tanyeli, Cihangir,Balci, Metin
, p. 453 - 456 (2007/10/03)
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.