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Updated: Jul 13, 2026

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
Published on: June 28, 2019
Highly stereoselective epoxidation of alpha-methyl-gamma-hydroxy-alpha,beta-unsaturated esters: rationalization and
Irakusne López1, Santiago Rodríguez, Javier Izquierdo
1Departament de Química Inorgànica i Orgànica Universitat Jaume I, 12080 Castelló, Spain.
Abstract:
The diastereoselectivity of the nucleophilic epoxidation of gamma-hydroxy-alpha,beta-unsaturated esters having a methyl substituent at the alpha- or beta-position was investigated. Epoxidation of the alpha-methyl-substituted enoate was highly stereoselective, giving rise to the syn isomer. This finding was used to perform an enantioselective synthesis of a natural product having a beta-hydroxy-alpha-methylene-gamma-butyrolactone motif. The nucleophilic epoxidation of enoates was found to be irreversible. Models to explain the observed stereoselectivities are proposed.
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