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有机化学
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有机化学 ›› 1997, Vol. 17 ›› Issue (5): 438-441. 上一篇    下一篇

研究论文

(-)-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

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。

关键词: 报警信息素, 碘代烃, 不对称反应, 烷基化, 其它基金, 磺酰胺 P, 庚酮 P, 脱硫, 内酰胺, 莰烷

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

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