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

doi:10.1016/S0040-4020(01)91971-4

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 journal › Article › peer-review

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 language	English
Pages (from-to)	2439-2444
Number of pages	6
Journal	Tetrahedron
Volume	39
Issue number	14
DOIs	https://doi.org/10.1016/S0040-4020(01)91971-4
Publication status	Published - 1983
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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.",

author = "Kenji Mori and Shigefumi Kuwahara and Hiraki Ueda",

year = "1983",

doi = "10.1016/S0040-4020(01)91971-4",

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AU - Mori, Kenji

AU - Kuwahara, Shigefumi

AU - Ueda, Hiraki

PY - 1983

Y1 - 1983

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AB - 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.

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