Tetrahedron letters

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 …

X Shi, WS Leal, Z Liu, E Schrader, J Meinwald

Index: Shi, Xiongwei; Leal, Walter Soares; Liu, Zhi; Schrader, Eric; Meinwald, Jerrold Tetrahedron Letters, 1995 , vol. 36, # 1 p. 71 - 74

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Citation Number: 65

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.