Microbial Oxidation of Chloroaromatics in the Enantiocontrolled Synthesis of Cyclitols: (-)-Dihydroconduritol C

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Abstract
(-)-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.

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