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Synlett 1991; 1991(4): 276-278
DOI: 10.1055/s-1991-20707
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New Synthesis of (d,l) cis-2-Desmethyl and 2,2-Di-desmethyl Chrysanthemic Acids

A. Krief* , D. Surleraux, M. J. Robson
  • *Facultés Universitaires Notre-Dame de la Paix, Department of Chemistry, 61 rue de Bruxelles, B-5000 Namur, Belgium
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Publication Date:
07 March 2002 (online)

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5-Substituted 2,2-dimethylcyclohexane-1,3-diones proved to be valuable precursors of (d,l) cis-chrysanthemic acid (3-isobutenyl-2,2-dimethyl-1-cyclopropanecarboxylic acid) and some of its analogues. The esters derived from the two stereoisomeric 2-desmethyl cis-chrysanthemic acids and 3-phenoxybenzaldehyde cyanohydrin [2-hydroxy-2-(3-phenoxyphenyl)acetonitrile] have been tested against three species of insects. The cyclopropyl ester with all three substituents cis to one another was found to be the most active.