Exploration On The Synthesis Of Sex Pheromones Of Anoplophora Leucoderma And Potato Tuber Mot

Green biological control plays a pivotal role in the prevention and control of plant diseases and insect pests.White spotted star beetle and potato tuber moth are two important pests that seriously harm the growth of woody plants and potato production in China,and the two insect sex pheromone do not contain or contain multiple chiral carbon atoms of long chain aliphatic compound.The current prevention and control measures mainly rely on traditional pesticides,which seriously restricts the protection of related forests and the benefits of crops.In this thesis,the chemical synthesis and biological activity of sex pheromones from two pests,the white spotted star beetle and the potato tuber moth,were studied.First of all,a key strategy for the complete synthesis of the sex pheromone gomadalactone A from the white spot beetle,oxy-Nazarov electrocyclization reaction,was developed.During the synthesis process,the Horner-Wadsworth-Emmons alkylation reaction was used twice to achieve the growth of the carbon chain and the construction of conjugated diene esters.In addition,the core hydroxycyclopentenone unit was constructed through the oxy-Nazarov electrocyclization reaction under the action of the reducing agent DIBAL-H.In the subsequent route,the double ring core skeleton and part of the carbon chain were grown through Grignard addition and oxidative etherification reactions.Although the total synthesis of the target molecule has not yet been completed,the above progress has laid a foundation for the subsequent growth of alkyl side chains and the construction of lactone rings.Secondly,under the guidance of the core idea of new uses of old reactions,traditional classical reactions were ingeniously applied to the total synthesis of two Sex pheromones of potato tuber moth,(4E,7Z)-tridecadienol acetate and(4E,7Z,10Z)-tridecatrienol acetate,which have the characteristics of polyene.A strategy using Lindlar catalytic hydrogenation to construct a Z type double bond and Stille coupling to stereoselectively construct an E type double bond was established as the key steps,The construction of the above two target molecules has been successfully achieved.The two synthesized sex pheromones were applied to field trapping experiments,and the results showed that the control effect was significant.In summary,this thesis developed a concise and efficient synthesis strategy to construct the core skeleton of the sex pheromone gomadalactone A of the white spotted star beetle,completed the complete synthesis of the sex pheromones(4E,7Z)-tridecadienol acetate and(4E,7Z,10Z)-tridecatrienol acetate of the potato tuber moth,and preliminarily explored the field control effects of these two pheromones.