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

Abstract

(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

CLC Number:

O627

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Huang Jinxia;Li Yan;Ma Xingquan;Ren Jun. Bornanesultam-directed synthesis of enantiomers of the alarm pheromone of the grematogaster ant[J]. Chin. J. Org. Chem., 2001, 21(4): 285-288.

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(S)的(R)吉尼斯蚁警戒素合成方法研究

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

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