Synthesis of all of the four possible stereoisomers of 4,8-dimethyldecanal, the aggregation pheromone of the flour beetles

Kenji Mori, Shigefumi Kuwahara, Hiraki Ueda

Research output: Contribution to journalArticle

62 Citations (Scopus)

Abstract

The four stereoisomers of 4,8-dimethyldecanal were synthesized employing organometallic or electrolytic coupling reactions as the key-step. The response of the red flour beetle, Tribolium castaneum, to the (4R, 8R)-isomer was identical with that to the natural pheromone, while other isomers induced only very weak or no responses. The (4R, 8R)-isomer is therefore the natural pheromone.

Original languageEnglish
Pages (from-to)2439-2444
Number of pages6
JournalTetrahedron
Volume39
Issue number14
DOIs
Publication statusPublished - 1983
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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