Fungal Strains as Catalysts for the Biotransformation of Halolactones by Hydrolytic Dehalogenation with the Dimethylcyclohexane System

Abstract

Bicyclic chloro-, bromo- and iodo-γ-lactones with dimethylcyclohexane rings were used as substrates for bioconversion by several fungal strains (<em>Fusarium</em>, <em>Botrytis</em> and <em>Beauveria</em>). Most of the selected microorganisms transformed these lactones by hydrolytic dehalogenation into the new compound <em>cis</em>-2-hydroxy-4,6-dimethyl-9-oxabicyclo[4.3.0]- nonan-8-one, mainly the (−)-isomer. When iodo-γ-lactone was used as the substrate, two products were observed: a hydroxy-γ-lactone and an unsaturated lactone. The structures of all substrates and products were established on the basis of their spectral data. The mechanism of dehalogenation of three halolactones was also studied.

Keywords

• lactones
• biotransformation
• hydrolytic dehalogenation
• &lt;em&gt;Fusarium&lt;/em&gt; species