Journal
TETRAHEDRON LETTERS
Volume 50, Issue 33, Pages 4738-4740Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.06.027
Keywords
Lepidopteran sex pheromone; Polyenyl hydrocarbons; GC-EAD analysis; Diimide reduction
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Funding
- Ministry of Education, Culture, Sports, Science, and Technology of Japan [20380031]
- Grants-in-Aid for Scientific Research [20380031] Funding Source: KAKEN
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(6Z,9Z,12Z)-6,9,12-Octadecatriene and (3Z,6Z,9Z,12Z)-3,6,9,12-icosatetraene, hydrocarbons unsaturated more highly than usual lepidopteran Type II pheromones, were identified from geometrid females of Hemithea tritonaria and Thalassodes immissaria intaminata, respectively. The triene was synthesized by a double Wittig reaction between hexanal and an ylide derived from (Z)-1,6-diiodo-3-hexene, and the tetraene was synthesized by a coupling between (Z)-3-undecenal and an ylide derived from (3Z,6Z)-1-iodo-3,6-nonadiene. Each synthetic compound attracted males of the corresponding emerald moths in a field. (C) 2009 Elsevier Ltd. All rights reserved.
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