Deciphering the Absolute Configuration of the Sex and Aggregation Pheromone of the Rice Stink Bug, Mormidea v-luteum

Six compounds specific to males were discovered as the sex-aggregation pheromone of the rice pest Mormidea v-luteum, including ttwo isomers of zingiberenol, three isomers of murgantiol, and the biosynthetic precursor, sesquipiperitol. To determine the absolute configuration of these compounds, a methodology involving synthetic approaches and microderivatizations in the natural product was employed. This was followed by enantiomeric resolution on a GC using a chiral stationary column.