An Alternative Method for the Synthesis of Female Sex Pheromone of the Citrus Mealybug, Planococcus citri

• Main Authors: Albert James Pape, 艾伯特
• Other Authors: Yao-Pin Yen
• Format: Others
• Language: zh-TW
• Published: 2015
• Online Access: http://ndltd.ncl.edu.tw/handle/27814014293955241922

碩士 === 靜宜大學 === 應用化學系 === 104 === A new synthetic route to the sex pheromone of the female citrus mealybug (Planococcus citri) is developed. Starting from (+)-α-pinene (11), Pd-catalyzed allylic oxidation yields enone product 8. Ruthenium-catalyzed oxidative decarboxylation affords acid product 9. Olefination is accomplished using a Mg-TiCl4 bimetallic reagent to afford 10. Finally, reduction by LiAlH4 and acetylation with acetic anhydride gives final product (+)-cis-planococcyl acetate (cis-1). This procedure offers an alternative path to obtain the pheromone, which has application as an environmentally friendly alternative to pesticide use.