Syntheses of Racemic and Scalemic cis-Chrysanthemic Acid from β,γ-Unsaturated Cyclohexanol

Authors

  • Alain Krief,

    1. Laboratoire de Chimie Organique de Synthèse, Facultés Universitaires N.-D. de la Paix, 61 rue de Bruxelles, B-5000 Namur
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  • Stéphane Jeanmart,

    1. Laboratoire de Chimie Organique de Synthèse, Facultés Universitaires N.-D. de la Paix, 61 rue de Bruxelles, B-5000 Namur
    2. Syngenta Crop Protection Münchwilen AG, Schaffhauserstrasse CH-4332 Stein
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  • Humaira Y. Gondal,

    1. Laboratoire de Chimie Organique de Synthèse, Facultés Universitaires N.-D. de la Paix, 61 rue de Bruxelles, B-5000 Namur
    2. Chemistry Department, University of Sargodha, Pakistan
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  • Adrian Kremer

    Corresponding author
    1. Laboratoire de Chimie Organique de Synthèse, Facultés Universitaires N.-D. de la Paix, 61 rue de Bruxelles, B-5000 Namur
    2. Laboratoire de Chimie Organique et des Matériaux Supramoléculaires, Facultés Universitaires N.-D. de la Paix, 61 rue de Bruxelles, B-5000 Namur, (phone: +32-81-725415)
    • Laboratoire de Chimie Organique et des Matériaux Supramoléculaires, Facultés Universitaires N.-D. de la Paix, 61 rue de Bruxelles, B-5000 Namur, (phone: +32-81-725415)

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Abstract

2,2,5,5-Tetramethylcyclohexane-1,3-dione is a valuable starting-material precursor of cis-chrysanthemic acid. The (1S)-stereoisomer is a precursor of pyrethrin I, the most active natural insecticide from Chrysanthemum cinerariifolium, whereas the (1R)-stereoisomer is efficiently transformed to deltamethrin, the most active commercially available pyrethroid insecticide. Several intermediates have been identified and used with variable success for that purpose.

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