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Synlett 1990; 1990(6): 309-310
DOI: 10.1055/s-1990-21072
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Microbial Oxidation of Chloroaromatics in the Enantiocontrolled Synthesis of Cyclitols: (-)-Dihydroconduritol C

Tomas Hudlicky* , John D. Price, Hector Luna, Catherine M. Andersen
  • *Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24061, USA
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Publication Date:
08 March 2002 (online)

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(-)-Dihydroconduritol C has been prepared in six steps from chlorobenzene. Complete stereochemical control in establishing the absolute configuration of the four chiral centers of the molecule was achieved. The key step is the microbial oxidation of chlorobenzene by Pseudomonas putida to afford (1S, 2S)-3-chloro-3,5-cyclohexadiene-1,2-diol with the requisite cis-stereochemistry of the hydroxyls.