Chemoenzymatic Synthesis of the C-13 Side Chain of Taxol: Optically Active 3-Hydroxy-4-phenyl β-Lactam Derivatives

Article abstract of DOI:10.1021/jo00057a018

Enantiomerically pure 3-hydroxy-4-phenyl β-lactam derivatives have been successfully prepared via enantioselective hydrolyses and transesterifications of racemic esters and alcohols respectivily catalyzed by bacterial lipases.These lipases also catalyzed highly enantioselective cleavage of the β-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.