A Novel Lepidopteran Sex Pheromone Produced by Females of a Lithosiinae Species,Lyclene dharma dharma, in the Family of Arctiidae

Improved Synthesis of Three Methyl-Branched Pheromone Components Produced by the Female Lichen Moth

“…2 enable three 2-ketones I-III to be synthesized in 18-58% total yields, while our previous syntheses achieved less than 10% total yields. 4,5) The GC-MS data for new synthetic I-III coincided well with those of the corresponding natural pheromone components, and the NMR data were the same as those of the compounds previously synthesized. 4,5,12) 14-Methyl-1-octadecene 2, our synthetic intermediate for II, is a pheromone component of the peach leafminer moth, Lyonetia clerkella L. (Lyonetiidae).…”

“…The structures were estimated by GC-MS analyses of the pheromone gland extracts before and after Wollf-Kishner reduction. 4) Although the absolute configurations of their chiral centers could not be determined because of the difficulty collecting a sufficient amount of the pheromone extract, the planar structures of I-III were confirmed by the synthesis regardless of their stereochemistry. The mass spectrum of each synthetic ketone coincided well with that of the corresponding natural component.…”

“…The mass spectrum of each synthetic ketone coincided well with that of the corresponding natural component. 4,5) Furthermore, lures baited with the optically inactive synthetic ketones successfully attracted many L. d. dharma males in the field. 5) L. d. dharma belongs to Lithosiinae in the family of Arctiidae and is the first species whose sex pheromone has been revealed among the species in this subfamily.…”

“…In our previous study, three components were separately synthesized by routes that started from diols of different chain length and involved no common synthetic units. 4,5) To obtain a sufficient amount of the synthetic pheromone, we investigated methods for increasing the yields of the three components. This report presents new synthetic routes for I-III via Wacker oxidation of the terminal alkenes which were constructed with common synthetic units.…”

Synthesis of All the Stereoisomers of 6-Methyl-2-octadecanone, 14-Methyl-2-octadecanone, and 6,14-Dimethyl-2-octadecanone, Sex Pheromone Components of theLyclene dharma dharmaMoth, from the Enantiomers of Citronellal

“…2) They then synthesized mixtures of all the possible stereoisomers of 1, 2, and 3, 2,3) and found that a mixture of 1, 2 and 3 in a ratio of 2:1:1 as well as a 2:1 mixture of 1 and 2 were pheromonally active, showing that 3 was not indispensable for bioactivity.…”