(-)-莰烷磺内酰胺法合成(S)和(R)切叶蚁警界信息素

本文以樟脑衍生物(-)-莰烷磺内酰胺(2)为原料，经N-烷酰基莰烷-2,10-磺内酰胺(3)与碘代烷的不对称烷基化反应，用二锂代乙基苯基砜取代磺内酰胺助剂以及铝汞还原性脱硫反应等三步合成(S)和(R)-切叶蚁警界信息素(1)，其光学纯度高达95%e.e.以上。

Bornanesultam-directed synthesis of (S) and (R) the alarm pheromone of the leaf-cutting ant

In this paper, (S) and (R)-4-methyl-3-heptanone (1), one of the alarm pheromone of the leaf-cutting ant (Atta texana and Atta cephalotes), was synthesized from R-(+)-camphor derivative N-bornane-2,10-sultam (2) via asymmetric alkylation of N- acylbornane-2,10-sultam (3) with alkyl iodide, displacement of the sultam auxiliary with dilithiated ethyl phenyl sulfone and reductive desulfurization with aluminium amalgam. The enantiomeric excess of the total synthesis is over 95% e.e.