Synthesis of all four stereoisomers of 6,10,13-trimethyltetradecan-2-one, a sex pheromone component produced by males of the stink bug Pallantia macunaima.
Synthesis of all four stereoisomers of 6,10,13-trimethyltetradecan-2-one, a sex pheromone component produced by males of the stink bug Pallantia macunaima.
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6,10,13-三甲基十四烷-2-酮的所有四种立体异构体的合成，这是雄性臭虫 Pallantia macunaima 产生的一种性信息素成分。
DOI：
10.1002/ejoc.201201688
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发表时间：
2013
期刊：
影响因子：
--
通讯作者：
and Tetsu ANDO
中科院分区：
文献类型：
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作者：
Yuta MURAKI;Tomonori TAGURI;Masanobu YAMAMOTO;Paulo H. G. ZARBIN;and Tetsu ANDO
Pallantia macunaima（异翅亚目：蝽科）是巴西南部的一种大豆害虫，雄性产生6，10，13-三甲基十四烷-2-酮与雌性交流。性信息素的所有四种立体异构体都是通过偶联两种手性结构单元合成的，这两种结构单元是使用仲甲苯磺酸酯的立体特异性转化作为关键反应从（S）-和（R）-环氧丙烷合成的。通过手性HPLC分析确认结构单元的对映体纯度。
The stink bugPallantia macunaima(Heteroptera: Pentatomidae) is a soybean pest in southern Brazil, and the males produce 6,10,13‐trimethyltetradecan‐2‐one to communicate with females. All four stereoisomers of the sex pheromone were synthesized by coupling two chiral building blocks, which were synthesized from (S)‐ and (R)‐propylene oxides using stereospecific inversion of secondary tosylates as a key reaction. The enantiomeric purities of the building blocks were confirmed by chiral HPLC analysis.