锈赤扁谷盗聚集信息素组分(S,Z)-十二碳-3-烯-11-内酯的全合成

Total Synthesis of (S,Z)-dodec-3-en-11-olide, An Aggregation Pheromone Component of Cryptolestes Ferrugineus

报道了仓储害虫锈赤扁谷盗的聚集信息素成分(S,Z)-十二碳-3-烯-11-内酯(1)的全合成。以6-溴-1-己醇为起始原料,通过手性环氧丙烷引入手性,经Wittig反应构建了关键的顺式双键,然后通过Mitsunobu反应合成1, 8步反应总产率10%,对映选择性99%。采用类似路线,选择另一种构型的手性环氧丙烷,合成了1的对映异构体大眼锯谷盗聚集信息素组分(R,Z)-十二碳-3-烯-11-内酯,其结构经~1H NMR,^(13)C NMR, IR和HR-MS(ESI)确证。

The total synthesis of ( S,Z )-dodec-3-en-11-olide( 1 ), a aggregation pheromone component of Cryptolestes ferrugineus , was reported in this paper. 6-Bromo-1-hexanol was chosen as the starting material, and the desired chirality for the final product was introduced by using the corresponding chiral propylene oxide. Wittig reaction was used to construct the cis -double bond, and Mitsunobu reaction was employed for cyclization to form dodecenolide. The total yield of 8 steps of reaction was 10% with 99% enantioselectivity. Similarly, by employing the same synthetic route and using a propylene oxide with the opposite chirality,( R,Z )-dodec-3-en-11-olide( 17 ), an aggregation pheromone component of Oryzaephilus mercator (Fauvel), has also been synthesized. The structures were confirmed by ^1H NMR,^13C NMR, IR and HR-MS(ESI).