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

K. Mori, S. Kuwahara, H. Z. Levinson, A. R. Levinson

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48 Citations (Scopus)

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).

Original languageEnglish
Pages (from-to)2291-2297
Number of pages7
JournalTetrahedron
Volume38
Issue number15
DOIs
Publication statusPublished - 1982
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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