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

doi:10.1016/0040-4039(94)02214-V

Tetrahedron Letters

Volume 36, Issue 1, 2 January 1995, Pages 71-74

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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.

Supellapyrone (1) can be synthesized by direct coupling of a bromopyrone (i) with an alkylzinc reagent (ii). The absolute configuration of the pheromone has been assigned as $(2′R,4′R)- 1$ .