1083308-99-9

Upstream product

• 1083308-98-8 (1S,6R)-2,2,5,5-tetramethyl-7-oxabicyclo[4.1.0]heptan-3-one 
• 1083309-00-5 C₁₀H₁₉BrO₂ 
• 13855-90-8 2,2,5,5-tetramethylcyclohex-3-en-1-one 
• 702-50-1 2,2,5,5-tetramethylcyclohexa-1,3-dione 
• 15500-76-2 Dimethyl-dimedon-mono-(toluol-4-sulfonyl-hydrazon) 
• 1083308-96-6 (1S)-2,2,5,5-tetramethylcyclohex-3-en-1-ol 
• 1083308-97-7 (1S,3S,6R)-2,2,5,5-tetramethyl-7-oxabicyclo[4.1.0]heptan-3-ol 

Relevant academic research and scientific papers

Syntheses of racemic and scalemic cis-chrysanthemic acid from β,γ-unsaturated cyclohexanol

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.

Selected regiocontrolled transformations applied to the synthesis of (1S)-cis-chrysanthemic acid from (1S)-3,4-epoxy-2,2,5,5-tetramethylcyclohexanol

(1S)-cis-Chrysanthemic acid has been prepared in a few steps with complete control of the relative and absolute stereochemistry using regiocontrolled epoxide ring opening, diol mono-oxidation and cyclopropanation. The Royal Society of Chemistry.

Diastereoselective epoxidation of compound bearing a cyclohex-3-enol moiety: Application to the enantioselective synthesis of (1R)-trans-chrysanthemic acid and (1R)-cis-deltametrinic acid

We disclose the synthesis of enantiomeric (1S)-cis- and (1R)-cis-chrysanthemic acids precursors of S-bioallethrin and deltamethrin the most active indoor and outdoor insecticides respectively. It involves an original strategy which takes advantage of the complete stereocontrolled epoxidation of an homoallylalcohol and the synthesis in the same pot of precursors of each of the two enantiomers of cis-chrysanthemic acid, bearing functional groups possessing similar reactivity but having different structural behavior which allow their easy separation.