PRODUCTION OF OPTICALLY ACTIVE 3,4-DIHYDRO-3,4-EPOXY-2H-1-BENZOPYRAN COMPOUND AND SYNTHETIC INTERMEDIATE THEREFOR

摘要

PURPOSE:To readily obtain the subject compound useful as an intermediate for medicines at a low cost by reacting a specific compound with a chirally specified carboxylic acid (reactive derivative thereof). CONSTITUTION:(A) A compound expressed by formula I (R1 and R2 are H or 1-6C alkyl or R1 and R2 together form 2-5C alkylene; R3 and R4 are H, halogen, nitro, cyano, amino, 1-6C alkyl, benzoyl, naphthoyl, etc.; X is Br, Cl or I) is reacted with (B) a compound (reactive derivative thereof) expressed by formula II [Ar is phenyl, naphthyl, thienyl, furyl, pyridyl, etc.; C marked with * is (S)-(-)-or (R)-(+)-] to afford a compound expressed by formula III, which is then subjected to fractional crystallization, then hydrolytic reaction and cyclized to provide the objective compound expressed by formula IV.