Synthesis method of sex pheromone (S)-14-methyl-1-octadecene of lepidoptera pest peach leaf miners

Abstract

The invention discloses a synthesis method of a sex pheromone (S)-14-methyl-1-octadecene of peach leaf miners, which comprises the following steps: carrying out ring opening on gamma-butyrolactone asa raw material, reacting the gamma-butyrolactone with benzyl chloride to generate 4-benzyloxybutyric acid, and reacting the 4-benzyloxybutyric acid with (S)-4-benzyl-2-oxazolidinone; performing reaction with methyl iodide under the action of organic base to induce chiral methyl; reducing the chiral methyl into alcohol under the action of lithium aluminum hydride, oxidizing the alcohol into aldehyde, and carrying out wittig reaction with triphenylpropylphosphonium bromide; after the Wittig reaction, using a Pt / C as a catalyst for catalytic hydrogenation to remove double bonds, removing benzyl with Pd / C as a catalyst to form alcohol, and oxidizing the alcohol into aldehyde; carrying out monobromination on 1, 10-decanediol, carrying out single protection by using TBSCl, and performing reaction with triphenylphosphine to obtain quaternary phosphonium salt; carrying out Wittig reaction on the aldehyde and the quaternary phosphonium salt, and using Pt / C as a catalyst for catalytic hydrogenation to eliminate double bonds; removing TBS single protection to form alcohol, and then oxidizing the alcohol into aldehyde; and reacting the aldehyde with methyltriphenylphosphonium bromide wittig toobtain the pheromone (S)-14-methyl-1-octadecene. According to the method, the reaction conditions are mild, chiral methyl is kept in the reaction process, and racemization is avoided.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis. Specifically, it is a method for synthesizing the sex pheromone (S)-14-methyl-1-octadecene of the Lepidoptera pest Peach leafminer. Background technique [0002] The peach leafminer Lyonetia clerkella L. is a common pest of the Lepidoptera Lepidoptera family. It is an important pest on peach leaves. Generational overlap is common and multiple insect states coexist. The peach leaf miner has about 7 generations every year. After hatching, the larvae feed on the leaf tissue and form curved borer passages. The leaf epidermis is not broken and can be seen through the leaf surface, which affects the normal physiological activities of the leaf and causes it to die and fall off. [0003] Insect pheromones have the following advantages: unique mode of action, high biological activity, and strong specificity; pests are not easy to develop drug resistance, and are harmless to natural enemies; si...

AI Technical Summary

Problems solved by technology

[0010] There are still many methods for synthesizing the sex pheromone of the peach leaf miner, but all of them have shortcomings such as too long steps or expensive raw materials.

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