A new synthesis of alkylated 2H-pyran-2-ones and its application to the determination of the relative and absolute configuration of supellapyrone, sex pheromone of the brownbanded cockroach, Supella longipalpa

Abstract

The sex pheromone of the brownbanded cockroach, Supella longipalpa, can be synthesized by direct coupling of a brominated pyrone with an alkylzinc reagent. The stereochemistry of the natural pheromone has been assigned as (2′R, 4′R)-5-(2′,4′-dimethylheptanyl)-3-methyl-2H-pyran-2-one by a combination of synthesis, chiral gas chromatography, and electrophysiological measurement.