Improved Synthesis of Three Methyl-Branched Pheromone Components Produced by the Female Lichen Moth
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概要
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Female moths of Lyclene dharma dharma (Arctiidae, Lithosiinae) produce a novel sex pheromone composed of three methyl-branched ketones: 6-methyl-2-octadecanone (I), 14-methyl-2-octadecanone (II), and 6,14-dimethyl-2-octadecanone (III). Their structures were confirmed by syntheses accomplished by a different route for each component. In order to obtain a sufficient amount of the synthetic pheromone, we developed new routes via methyl-branched 1-alkenes: 6-methyl-1-octadecene (1), 14-methyl-1-octadecene (2), and 6,14-dimethyl-1-octadecene (3). Compound 1 was synthesized by coupling between a C10-chain bromide and a 3-methyl-branched C8 unit (A) prepared from 3-methyl-1,5-pentanediol, 2, by coupling between a C11-chain bromide and a 3-methyl-branched C7 unit (B) prepared from 2-hexanone, and 3, by connecting A and B, using propargyl alcohol as a C3 linchpin. The use of 3-chloro-1-propanol and tert-butyl acetoacetate as the linchpin was also examined to connect the two synthetic blocks in the synthesis of 3. Components I–III were obtained by Wacker oxidation of the corresponding 1-alkenes 1–3 in good yields.
- 社団法人 日本農芸化学会の論文
著者
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Yamakawa Rei
Graduate School of Bio-Applications and Systems Engineering (BASE), Tokyo University of Agriculture
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ANDO Tetsu
Graduate School of Bio-Applications and Systems Engineering (BASE), Tokyo University of Agriculture
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Taguri Tomonori
Graduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Tec
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ADACHI Yasushi
Graduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Tec
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MORI Kenji
Photosensitive Materials Research Center, Toyo Gosei Co., Ltd.
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