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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. |