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Synthesis 1996; 1996(7): 823-825
DOI: 10.1055/s-1996-4305
short paper
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Lipase-Catalyzed Optical Resolution of (1RS,7RS)-2-Oxotricyclo[2.2.1.03,5]heptane-7-carboxylic Acid Methyl Ester: Precursor for Large Scale Synthesis of Non-Racemic Prostaglandins

E. Wolfgang Holla* , Heinz-Peter Rebenstock, Bernd Napierski, Gerhard Beck
  • *Hoechst AG, Zentrale Pharmaforschung, Postfach 800320, D-65926 Frankfurt/Main, Germany, Fax +49(69)331399
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Publication Date:
31 December 2000 (online)

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As a result of screening several lipases, esterases and proteases for the ability to resolve ester derivatives of the racemic title compound rac -2, a lipase-catalyzed enantioselective hydrolysis of methyl ester rac -4 was developed on a 200 g scale. Exposure of the readily available racemic bicyclo[2.2.1]heptane derivative rac -4 to thermostable lipase SP 526 from Candida antarctica in buffered solution affords the desired (+)-enantiomer as (remaining) ester 4 with ≥ 99% enantiomeric excess in 82% yield.

optical resolution - enzymatic hydrolysis - Candida antarctica lipase SP 526 - bicyclo[2.2.1]heptane derivative - prostaglandin precursor