Tetrahedron letters

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

SJ Maddrell, NJ Turner, A Kerridge, AJ Willetts…

Index: Maddrell, Samuel J.; Turner, Nicholas J.; Kerridge, Alison; Willetts, Andrew J.; Crosby, John Tetrahedron Letters, 1996 , vol. 37, # 33 p. 6001 - 6004

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Citation Number: 57

Abstract

(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% ee), 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.