Sequential enzymatic and electrochemical functionalization of bromocyclohexadienediols: Application to the synthesis of (-)-conduritol C
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Abstractcis-Diene diol obtained from the microbial oxidation of bromobenzene was used as a substrate for the chemoenzymatic acetylation and epoxidation with lipases. The model studies showed that the regiochemistry of the acetylation is solvent-dependent. The chemoenzymatic epoxidation followed the expected regiochemistry when compared to the chemical epoxidation with m-CPBA, but with the unexpected formation of bromoconduritol-C, an important intermediate whose electrochemical reduction led to the synthesis of (-)-conduritol-C. Experimental and spectral data are provided for all new compounds.