Synthesis and biological activity of both (E)- and (Z)-isomers of optically pure (S)-14-methyl-8-hexadecenal (trogodermal), the antipodes of the pheromone of the khapra beetle

doi:10.1016/0040-4020(82)87005-1

Tetrahedron

Volume 38, Issue 15, 1982, Pages 2291-2297

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Abstract

Both (E)- and (Z)-isomers of (S)-14-methyl-8-hexadecenal (trogodermal) were synthesized from 100% optically pure (R)-(+)-citronellic acid. These antipodes of the khapra beetle pheromone were 1/500 to 1/1000 times as active as the natural (R)-pheromone. Determination of the optical purities of citronellic acid and related compounds was achieved by hplc method. Warning was made not to forget the measurement of density in expressing the optical rotation of a neat liquid as [α]_D (neat).

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Synthesis and biological activity of both (E)- and (Z)-isomers of optically pure (S)-14-methyl-8-hexadecenal (trogodermal), the antipodes of the pheromone of the khapra beetle

Abstract

Tetrahedron Letters

Tetrahedron

Agric. Biol. Chem.

Tetrahedron

Naturwissenschaften

Tetrahedron

Tetrahedron

Agric. Biol. Chem.

Naturwissenschaften

Tetrahedron

Tetrahedron

Science

J. Chem. Ecol.