Unsymmetrical double Wittig olefination on the syntheses of insect pheromones. Part 1: Synthesis of 5,9-dimethylpentadecane, the sexual pheromone of Leucoptera coffeella
作者:Paulo H.G. Zarbin、Jefferson L. Princival、Eraldo R. de Lima、Alcindo A. dos Santos、Bianca G. Ambrogio、Alfredo R.M. de Oliveira
DOI:10.1016/j.tetlet.2003.10.183
日期:2004.1
three-step synthesis of a mixture of stereoisomers of 5,9-dimethylpentadecane 1, the sexual pheromone of the coffee leaf miner Leucoptera coffeella, is described. The route employs an unsymmetrical double Wittig olefination to build the carbon skeleton of the molecule, as the key reaction. The bis-phosphonium salt 3, derived from 1,3-dibromopropane 2, reacted ‘one-pot’ with the ketones 2-octanone and
描述了一种快速的三步合成5,9-二甲基十五烷1的立体异构体混合物的方法,该混合物是咖啡叶矿工Leucoptera coffeella的有性信息素。该路线采用不对称的双重维蒂希(Wittig)烯化反应来构建分子的碳骨架,这是关键反应。衍生自1,3-二溴丙烷2的双phosph盐3与酮2-辛烷酮和2-己酮“一锅”反应,得到不对称二烯4。将其容易地在Pd / C上氢化,以54%的总产率提供信息素1。合成1在野外实验中显示出高生物活性。