Syntheses of Racemic and Scalemic cis‐Chrysanthemic Acid from β,γ‐Unsaturated Cyclohexanol |
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| Authors: | Alain Krief Stéphane Jeanmart Humaira Y. Gondal Adrian Kremer |
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| Affiliation: | 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;3. Chemistry Department, University of Sargodha, Pakistan;4. 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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| Keywords: | Dibromination Epoxidation Carbocyclization Pyrethroids |
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