APPLICATION OF LIPASE-CATALYZED TRANSFORMATIONS FOR THE SYNTHESIS OF INSECT PHEROMONES AND RELATED-COMPOUNDS

This review describes efficient means of preparing optically pure inse ct pheromones and related compounds via lipase-catalyzed enantioselect ive reaction on a large scale. (1) A new synthesis of the Japanese bee tle pheromone, (R,Z)-(-)-5-(1-decenyl)oxacyclopentan-2-one, establishe d by a combination of two lipase-catalyzed transformation was demonstr ated. (2) A chemico-enzymatic procedure for the syntheses of both enan tiomers of cupreous chafer beetle pheromone, (R,Z)- and (S,Z)-5-(1-oct enyl)oxacyclopentan-2-one, was described. (3) An optical resolution of (+/-)-2,3-epoxy-8-methyl-1-nonanol, the key intermediate of the synth esis of gypsy moth pheromone, was demonstrated. (4) A practical chemic o-enzymatic synthesis of (+)-disparlure in large scale was demonstrate d. (5) A facile synthesis of carboxyalkyl acrylate, which is special m onomers in the synthesis of the new polymers, by two lipase-catalyzed regioselective reactions was described.