Chin. J. Org. Chem. ›› 1997, Vol. 17 ›› Issue (5): 438-441. Previous Articles     Next Articles

Original Articles

(-)-莰烷磺内酰胺法合成(S)和(R)切叶蚁警界信息素

李焰;黄锦霞;方国苏;陈祖兴;徐章煌   

  1. 湖北大学化学系
  • 发布日期:1997-10-25

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

LI YAN;HUANG JINXIA;FANG GUOSU;CHEN ZUXING;XU ZHANGHUANG   

  • Published:1997-10-25

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.

Key words: ALARM PHEROMONE, IODOHYDROCARBON, DESULFURIZATION, HEPTANONE P, SULFAMIDE P, LACTAM, BORNANE, ALKYLATION

CLC Number: