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Synlett 1995; 1995(8): 806-808
DOI: 10.1055/s-1995-5099
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Unusual Dehalogenation of a Bridgehead Halide. Biocatalytic Conversion of Halocyclohexadiene-cis-diols to the trans-Isomers and Synthesis of Optically Pure Cyclohexadiene-trans-diols

Bryan P. McKibben, George S. Barnosky, Tomas Hudlicky*
  • *Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, VA 24061-0212, USA
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Publication Date:
31 December 2000 (online)

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An enantioselective synthesis of cyclohexadiene-trans-diols from the microbially derived cis-isomers is described. The synthesis features a general route to the production of bromo-, chloro- and cyclohexadiene-trans-diols. The key feature in the cis/trans conversion is the cycloaddition/cycloreversion sequence utilized to protect and deprotect the sensitive 1,3-diene system.

cycloaddition - cycloreversion - cyclohexadiene-cis-diols - cyclohexadiene-trans-diols