Chinese Journal of Organic Chemistry 2001, 21(4) 285-288  DOI:     ISSN: 0253-2786 CN: 31-1321/O6

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Keywords
CAMPHOR
SULTONE
BORNANE
LACTAM P
ADDITION REACTION
MANNICH REACTION
ALARM PHEROMONE
GRIGNARD REACTION
SYNTHESIS METHODS
Authors
Huang Jinxia
Huang Jinxia
Huang Jinxia
Li Yan
Li Yan
Li Yan
Ma Xingquan
Ma Xingquan
Ma Xingquan
Ren Jun
Ren Jun
Ren Jun
PubMed
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Bornanesultam-directed synthesis of enantiomers of the alarm pheromone of the grematogaster ant

Huang Jinxia;Li Yan;Ma Xingquan;Ren Jun

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.

Keywords CAMPHOR   SULTONE   BORNANE   LACTAM P   ADDITION REACTION   MANNICH REACTION   ALARM PHEROMONE   GRIGNARD REACTION   SYNTHESIS METHODS  
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