CHEMOENZYMATIC SYNTHESIS OF THE C-13 SIDE-CHAIN OF TAXOL - OPTICALLY-ACTIVE 3-HYDROXY-4-PHENYL BETA-LACTAM DERIVATIVES

Enantiomerically-pure 3-hydroxy-4-phenyl beta-lactam derivatives have been successfully prepared via enantioselective hydrolyses and transesterifications of racemic esters and alcohols respectively catalyzed by bacterial lipases. These lipases also catalyzed highly enantioselective cleavage of the beta-lactam ring of (+/-)-10 to yield derivatives of (2R,3S)-phenylisoserine in high enantiomeric excess. The resolved enantiomers are important intermediates in the synthesis of the C-13 side chain of taxol.