Synthesis of (1R,3S,5S)-1,3,8-Trimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene, the Male Pheromone of a Hepialid Moth Endoclita excrescens, and Its Enantiomer

Both (1R,3S,5S)- and (1S,3R,5R)-isomers of 1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene were synthesized by starting from (S)- and (R)-isomers of ethyl 3-hydroxybutanoate, respectively. The (1R,3S,5S)-isomer was identified as the male sex pheromone of a Japanese hepialid moth, Endoclita excresce...

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Published in:Chemistry letters 2002-01, Vol.31 (1), p.40-41
Main Authors: Marukawa, Kaoru, Mori, Kenji
Format: Article
Language:English
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Summary:Both (1R,3S,5S)- and (1S,3R,5R)-isomers of 1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene were synthesized by starting from (S)- and (R)-isomers of ethyl 3-hydroxybutanoate, respectively. The (1R,3S,5S)-isomer was identified as the male sex pheromone of a Japanese hepialid moth, Endoclita excrescens.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2002.40