Nitrile hydratase enzymes in organic synthesis: Enantioselective synthesis of the lactone moiety of the mevinic acids

Article abstract of DOI:10.1016/0040-4039(96)01259-2

(R)-4-Hydroxy-5-cyanopentene (-)-9, a known precursor of the protected lactone moiety of the mevinic acids 1, has been prepared in 9 steps from (S)-3-(benzyloxy)-4-cyanobutanoic acid 5 (88% e.e.) which was obtained by the asymmetric 2 step hydrolysis of 3-benzyloxyglutaronitrile 4 involving the successive activity of a nitrile hydratase and an amidase enzyme.