Synthesis of the four components of the female sex pheromone of the painted apple moth, Teia anartoides
- PMID: 12913301
- DOI: 10.1271/bbb.67.1559
Synthesis of the four components of the female sex pheromone of the painted apple moth, Teia anartoides
Abstract
Four pheromone components of the female painted apple moth (Teia anartoides), an Australian insect pest, were synthesized. These were (Z)-6-henicosen-11-one (1), (6Z, 8E)-6,8-henicosadien-11-one (2), (Z)-cis-9,10-epoxy-6-henicosene (3), and (Z)-cis-9,10-epoxy-6-icosene (4). 2-Dodecanone was converted to 1 and 2, and both the enantiomers of 3 and 4 were synthesized from the enantiomers of 4-tert-butyldimethylsilyloxy-cis-2,3-epoxy-1-butanol.
Similar articles
-
(Z,Z)-6,9-Heneicosadien-11-one: major sex pheromone component of painted apple moth, Teia anartoides.J Chem Ecol. 2005 Mar;31(3):603-20. doi: 10.1007/s10886-005-2048-z. J Chem Ecol. 2005. PMID: 15898504
-
Identification of sex pheromone components of the painted apple moth: a tussock moth with a thermally labile pheromone component.J Chem Ecol. 2005 Mar;31(3):621-46. doi: 10.1007/s10886-005-2050-5. J Chem Ecol. 2005. PMID: 15898505
-
New synthesis of the (3Z,6Z,9S,10R)-isomers of 9,10-epoxy-3,6-henicosadiene and 9,10-epoxy-1,3,6-henicosatriene, pheromone components of the female fall webworm moth, Hyphantria cunea.Biosci Biotechnol Biochem. 2005 May;69(5):1007-13. doi: 10.1271/bbb.69.1007. Biosci Biotechnol Biochem. 2005. PMID: 15914922
-
The potential direct impacts on human health resulting from the establishment of the painted apple moth (Teia anartoides) in New Zealand.N Z Med J. 2008 Jul 25;121(1278):35-40. N Z Med J. 2008. PMID: 18670468 Review.
-
Codling moth management and chemical ecology.Annu Rev Entomol. 2008;53:503-22. doi: 10.1146/annurev.ento.53.103106.093323. Annu Rev Entomol. 2008. PMID: 17877451 Review.
Cited by
-
(Z,Z)-6,9-Heneicosadien-11-one: major sex pheromone component of painted apple moth, Teia anartoides.J Chem Ecol. 2005 Mar;31(3):603-20. doi: 10.1007/s10886-005-2048-z. J Chem Ecol. 2005. PMID: 15898504
-
Identification of sex pheromone components of the painted apple moth: a tussock moth with a thermally labile pheromone component.J Chem Ecol. 2005 Mar;31(3):621-46. doi: 10.1007/s10886-005-2050-5. J Chem Ecol. 2005. PMID: 15898505
-
Asymmetric Synthesis of Three Alkenyl Epoxides: Crafting the Sex Pheromones of the Elm Spanworm and the Painted Apple Moth.Molecules. 2024 May 4;29(9):2136. doi: 10.3390/molecules29092136. Molecules. 2024. PMID: 38731627 Free PMC article.
-
Synthetic mycolates derivatives to decipher protein mycoloylation, a unique post-translational modification in bacteria.J Biol Chem. 2025 Mar;301(3):108243. doi: 10.1016/j.jbc.2025.108243. Epub 2025 Jan 27. J Biol Chem. 2025. PMID: 39880088 Free PMC article.