SYNTHESIS OF NORBORNENE FURYL ESTERS AND THEIR ENZYMATIC KINETIC RESOLUTION BY PIG LIVER ESTRASE (PLE)

Abstract
The reaction of furylacrylic acid with cyclopentadiene in toluene gave the
expected Diels-Alder endo-and exo-adductsin -1 : 1 ratio. The adducts were separated
by iodolactonization method to provide 3-endo-(2'-furyl) bicyclo 12.2.11 hept-5-ene-
2-exo-carboxylic acid and 3-exo-(2'-fury1)bicyclo 12.2.11 hept-5-ene-2-endocarboxylic
acid. Esterification of these acids by MeI / HMPA gave the expected
methyl esters. Kinetic resolution of racemic endo- and exo-ester adducts by
PLE(phosphate buffer, pH, 8) provided the related optically active isomers