Synthesis of the enantiomers of 5-hexadecanolide, the pheromone of the queen of the oriental hornet, vespa orientalis,employing enzymic resolution of (±)-2-aminotridecanoic acid as the key-step

Abstract

Optical resolution of(±)-2-chloroacetylaminotridecanoic acid with amino acylase gave (S)-2-aminotridecanoic add, which was converted into highly optically pure (S)-5-hexadecanolide (the pheromone of Vespa orientalls). Similarly (R)-2-chloroacetylammotridecanoic acid recovered after the enzymic hydrolysis yielded (R)-5-hexadecanolide. The existing methods for the preparation of the enantiomers of 5-hexadecanolide were critically surveyed to point out basic requisites for an effective chiral synthesis.