Lipase-catalyzed optical resolution of (1RS,7RS)-2-oxotricyclo[2.1.1.03,5]heptane-7-carboxylic acid methyl ester: Precursor for large scale synthesis of non-racemic prostaglandins

Article abstract of DOI:10.1055/s-1996-4305

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.