Asymmetric preparation of antifungal 1-(4′-chlorophenyl)-1-cyclopropyl methanol and 1-(4′-chlorophenyl)-2-phenylethanol. Study of the detoxification mechanism by Botrytis cinerea

Add time:07/13/2019    Source:sciencedirect.com

Chiral alcohols are important as bioactive compounds or as precursors to such molecules. On the basis of the different antifungal properties of the enantiopure alcohol derivatives of 4′-chlorophenyl cyclopropyl ketone and benzyl 4′-chlorophenyl ketone, their enantioselective synthesis by chemical and biocatalytic methods was studied. The detoxification pathways by the phytopathogen fungus Botrytis cinerea are reported.

► The antifungal compound (R)-1-(4′-chlorophenyl)-2-phenylethanol was prepared by means of treatment with (R)-methyl oxazaborolidine, with >99% ee and 98% yield, and by lipase-mediated acetylation, with 99% ee. ► The antifungal compound (S)-1-(4′-chlorophenyl)-2-phenylethanol was prepared by means of treatment with (S)-methyl oxazaborolidine, with >99% ee and 98% yield, and by baker's yeast fermentation, with 97% ee. ► The antifungal compound (R)-1-(4′-chlorophenyl)-1-cyclopropylmethanol was prepared by means of lipase-mediated hydrolysis, with 98% ee and 85.5% yield. ► The antifungal compound (S)-1-(4′-chlorophenyl)-1-cyclopropylmethanol was prepared by means of baker's yeast fermentation, with 96% ee and 12% conversion. ► Biotransformation of 1-(4′-chlorophenyl)-1-cyclopropylmethanol by the phytopathogen Botrytis cinerea shows the detoxification pathways by the fungus.

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