(-)-莰烷磺内酰胺法立体选择性合成米象虫和玉米象虫聚集合信息素

本文以(-)-莰烷-2, 10-磺内酰胺(2)为原料经六步反应立体选择性地合成了米象虫和玉米象虫聚集信息素(4S, 5R)-Sitophilure, 两个手性中心是由N-丙酰基-莰烷-2, 10-磺内酰胺(3)与丙醛进行的不对称顺式醛醇缩合反应一次性引入的。该全合成的对映异构体纯度可达96%e.e。

Bornanesultam-directed stereoselective synthesis of (4S, 5R)-sitophilure

(4S, 5R)-Sitophilure, the major component of the aggregation pheromone of the rice weevil and the maize weevil, was stereoselectively synthesized by six-step sequence starting from N-bornane-2, 10-sultam(2), the two asymmetric carbon atoms of the target product was achieved by employing asymmeric syn-aldolization of N-propionyl bornane-2, 10-sultam(3) with propylaldehyde. The enantiomeric excess of (4S, 5R)-Sitophilure prepared by this route is about 96%.