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Synthesis 1988; 1988(7): 540-541
DOI: 10.1055/s-1988-27630
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Synthesis of (1S,4R)-(-)-4-Hydroxy-2-cyclopentenyl Acetate by a Highly Enantioselective Enzyme-Catalyzed Transesterification in Organic Solvents

Fritz Theil* , Sibylle Ballschuh, Hans Schick, Monika Haupt, Barbara Häfner, Sigfrid Schwarz
  • *Central Institute of Organic Chemistry of the Academy of Sciences of the GDR, Rudower Chaussee 5, DDR-1199 Berlin, German Democratic Republic
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Publication Date:
18 September 2002 (online)

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(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 50%. The enantiomeric excess of the crude product was 95%. It could be raised to more than 99% by a single recrystallization. Commercially available pancreatin, a crude enzyme preparation from porcine pancreas, was used as biocatalyst.