CONVERSION OF INACTIVE STERIC ISOMER IN SYNTHETIC SERRICORNIN TO ACTIVE STERIC ISOMER

摘要

PURPOSE:To convert the inactive steric isomer in synthetic serricornin to the active steric isomer to increase the sex-attracting activity of the compound, by the epimerizing reaction treatment with an acid or base catalyst and/or a racemizing reaction treatment with a base catalyst. CONSTITUTION:The inactive steric isomers of formula II and formula III are separated from the mixture of steric isomers of formulas I -IV (the letters enclosed with represents the relative steric configuration of 4,6,7-position) of serricornin synthesized by a chemical synthesizing means. The separated inactive steric isomers are subjected to (a) the epimerization treatment with an acid or amine base and/or (b) the racemization treatment with a base catalyst such as metal hydroxide or metal alkoxide, etc. The isomer of formula II [in the case of the (a) process] or the isomer of formula III [in the case of the (b) process] can be converted to the active steric isomer of formula I effective as a sex attractant of cigarette beetle.