(4S)-4-苄基-2-噁唑烷酮诱导切叶蚁警戒信息素的合成

Synthesis of the alarm pheromone of the leaf-cutting ant using (4S)-4-benzyl-1,3-oxazolidin-2-one as chiral auxiliary

以(4S)-4-苄基-2-噁唑烷酮为手性助剂,与丙酰氯发生N-酰化反应,酰化产物与碘代正丙烷进行不对称烷基化反应,在NaBH4作用下氢解得到(S)-2-甲基-戊醇,再经氧化、格氏加成和氧化等反应,合成了切叶蚁警戒信息素,其化学总产率为30.98%,光学异构体纯度高达94%e.e.

（4S）-4-benyl-oxazoli-2-one, used as chiral auxiliary, was first N-acylated by propionyl chloride, and asymmetrical alkylated with iodopropane, followed by cleavage using NaBH4 to give （S）-2-methyl-pentanol, which ordinally proceeded oxidation, addition, oxidation, etc to successfully synthesize the alarm pheromone of the leaf-cutting ant. The total enantiomeric exess is over 94%e. e. and the total yield was up to 30.98 %.