Synthesis of (1S,4R)-(-)-40Hydroxy-2-cyclopentenyl Acetate by a Highly Enantioselective Enzyme-Catalyzed Transesterification in Organic Solvents

Article abstract of DOI:10.1055/s-1988-27630

(1S,4R)-(-)-4-Hydroxy-2-cyclopentenyl acetate (2), a versatile intermediate in prostaglandin syntheses, was readily prepared by an efficient enzyme-catalyzed enantioselective monoacetylation of cis-2-cyclopenten-1,4-diol (1) with 2,2,2-trichloroethyl acetate in the organic solvent system triethylamine/tetrahydrofuran.The chemical yield reached nearly 50percent.The enantiomeric excess of the crude product was 95percent.It could be raised to more than 99percent by a single recrystalization.Commercially available pancreatin, a crude enzyme preparation from porcine pancreas, was used as biocatalyst.