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


GÜLTEKİN M. S. , Celik M., TURKUT E., Tanyeli C. , BALCİ M.

TETRAHEDRON-ASYMMETRY, vol.15, no.3, pp.453-456, 2004 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 15 Issue: 3
  • Publication Date: 2004
  • Doi Number: 10.1016/j.tetasy.2003.11.037
  • Title of Journal : TETRAHEDRON-ASYMMETRY
  • Page Numbers: pp.453-456

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 OsO4 resulted in the formation of (-)-proto-quercitol and (+)-proto-quercitol, respectively. (C) 2003 Elsevier Ltd. All rights reserved.