基于资源化学品的黄星天牛信息素合成

Synthesis of the sex pheromone of yellow-spotted longicorn beetle based on strategy of resource chemistry

[目的]为了对黄星天牛综合治理以实现绿色林业,将性信息素应用于林间以防治该害虫,发展简便、经济的黄星天牛性信息素合成方法是非常必要的。[方法]采用C4+C12+C11+C8的汇聚式合成策略,通过Wittig反应,戴斯马丁氧化,Pd/C催化加氢,二醇选择性单保护,醇羟基碘取代等12步反应,实现了黄星天牛性信息素(R,Z)-21-甲基-8-三十五碳烯的全合成。[结果]产物中的手性中心碳来自于皂素工业资源性化合物,按该化合物计算,以25%的总收率立体合成了黄星天牛性信息素。[结论]为此种昆虫信息素提供了一种全新的合成方法,并且为此类含有立体碳碳双键及手性甲基侧链的昆虫信息素类化合物的合成提供了新的思路。

[Aims]It is highly necessary to develop a simple and economical synthetic method for the sex pheromone of the yellow-spotted longicorn beetle so that IPM can be implemented in green forestry.[Methods]Based on C4+C12+C11+C8 convergent strategy and through Wittig reaction,from Dess-Martin oxidation,Pd/C catalytic hydrogenation,monoselective protection of diols,iodine substitution of alcohols etc,by 12 steps all in all,an efficient synthesis of(R,Z)-21-methyl-8-pentatriacontene,the sex pheromone of yellow-spotted longicorn were achieved.[Results]The chiral carbon center of the compound was derived from a resource chemical coming from steroid industry.The total yield of this synthesis was 25%according to the chiral starting material.[Conclusions]It provides a new route for the synthesis of this insect pheromone and reveals a new strategy to these compounds which contain stereocarbon-carbon double bond and chiral methyl side chain structure.