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有机化学
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有机化学 ›› 2001, Vol. 21 ›› Issue (4): 285-288. 上一篇    下一篇

研究论文

(S)的(R)吉尼斯蚁警戒素合成方法研究

黄锦霞;李焰;马兴泉;任君   

  1. 湖北大学化学与材料科学学院
  • 发布日期:2001-04-25

Bornanesultam-directed synthesis of enantiomers of the alarm pheromone of the grematogaster ant

Huang Jinxia;Li Yan;Ma Xingquan;Ren Jun   

  • Published:2001-04-25

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以樟脑衍生物(-)-莰烷磺内酰胺为原料，经N-酰基莰烷-2,10-磺内酰胺与EtMgBr进行Michael加成反应，用氢化铝锂取代磺内酰胺助剂及溴化锂取代等步骤合成了(S)和(R)吉尼斯蚁警戒素，光学纯度达98%ee。

关键词: 吉尼斯蚁, 樟脑, 莰烷磺内酰胺, 磺内酯, 莰烷, 内酰胺P, 加成反应, 曼尼希反应, 不对称反应, 警戒素, 格氏反应, 合成法

(S) and (R)-6-methyl-3-octanone, one of the alarm pheromones of the Grematogaster ant, were synthesized from R-(+)-camphor derivatives N- bronane-2,10-sultams via conjugate addition of Grignard reagent to N- acylborane-2,10- sultam, reductive removal of the sultam auxiliary with lithium aluminum hydride and displacement with TsCl, LiBr and n- C3H5COCl. The enantiomeric excess of each final product was 98% ee.

Key words: CAMPHOR, SULTONE, BORNANE, LACTAM P, ADDITION REACTION, MANNICH REACTION, ALARM PHEROMONE, GRIGNARD REACTION, SYNTHESIS METHODS

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