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

M.Serdar Gültekin,Murat Çelik,Engin Turkut,Cihangir Tanyeli,Metin Balci

doi:10.1016/j.tetasy.2003.11.037

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

M.Serdar Gültekin, Murat Çelik + Show 3 more

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

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Journal: Tetrahedron: Asymmetry	Publication Date: Feb 1, 2004
Citations: 16

Affiliation: Atatürk University, Middle East Technical University

#Candida Cylindracea Lipase #Hydroperoxy Endoperoxide + Show 8 more

Abstract
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Abstract

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 OsO 4 resulted in the formation of (−)- proto-quercitol and (+)- proto-quercitol, respectively.

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