立体変換反応による光学活性菊酸の合成

抄録

In spite of recent development of pyrethroid insecticides, chrysanthemic acid still remain as an important intermediate for many synthetic pyrethroid insecticides. Chilarity of chrysanthemic acid determines the insecticidal activity, (+)-acid forming active ingredients. Among possible production methods of (+)-acid, optical resolution is advantageous to obtain optically pure acid. Major breakthrough has been accomplished by epimerization and racemization techniques. Thus, synthetic racemic chrysanthemic acid is optically resolved with (S)-1-phenyl-2-(p-tolyl) ethylamine to give (+)-chrysanthemic acid, and the residue, (-)-acid, is racemized to provide racemate. Other stereochemical studies have been conducted systematically aimed at stereochemical interconversion reactions, namely C1 and C3 epimerizations as well as racemization. Selective ring-opening reactions and the application were also studied. Some chiral perfumes were synthesized from optically active Chrysanthemic acid.