(5R,7R)-5-Methylheptadecan-7-ol: a novel sex pheromone component produced by a female lichen moth, Miltochrista calamina, in the family Arctiidae
作者:Rei Yamakawa、Ryutaro Kiyota、Tomonori Taguri、Tetsu Ando
DOI:10.1016/j.tetlet.2011.08.136
日期:2011.11
5-methylheptadecan-7-ol (1) as one possible structure. The four stereoisomers of 1 in a ratio of 4:4:1:1 were prepared from (S)-β-citronellol with 60% ee, and were separated by a combination of achiral and chiral HPLC columns. The absolute configuration of each isomer was determined by the comparison with the chromatographic behaviors of other samples synthesized by a different scheme, which applied the Jacobsen
在雌性地衣蛾Miltochrista calamina(Arctiidae,Lithosiinae)的信息素腺提取物中发现了甲基支化的十七烷醇。GC-MS分析了乙醇和随后通过甲磺酰氯和LiAlD 4的微处理反应衍生出的碳氢化合物,这是一种可能的结构,即5-甲基十七烷-7-醇(1)。的四种立体异构体1在4:1的比例:4:1:1,从(制备小号具有60%ee的)-β-香茅醇,并通过非手性和手性HPLC色谱柱分离。通过与通过不同方案合成的其他样品的色谱行为进行比较,可以确定每种异构体的绝对构型,这些方案应用了外消旋1,2-环氧十二烷的雅各布森水解动力学拆分来固定7-羟基的构型。只有(5 R,7 R)异构体吸引了雄蛾。因此,我们得出结论,Calamina雌性雌性分泌(5 R,7 R)-1作为性信息素,表明鳞翅目雌性性信息素是新的化学类别。