168416-28-2

Upstream product

• 41891-54-7 diethyl 3-(ethoxycarbonyl)-3-methylprop-2-en-yl phosphate 
• 168416-27-1 (R,S)-(2Z,4E)-3-methyl-5-(6-<13CD3>-2,6,6-trimethylcyclohex-1-en-1-yl)-2,4-pentadienenal 
• 638-10-8 ethyl 3-methylbut-2-enoate 
• 168416-22-6 <(R,S)-2-<13CD3>>-2,2,6-trimethylcyclohexanone 
• 168416-24-8 <(R,S)-6-<13CD3>>-2,6,6-trimethyl-1-cyclohexene-1-aldehyde 
• 168416-25-9 (R,S)-5,6-dihydro-4-methyl-6-<6-<13CD3>-2,6,6-trimethylcyclohex-1-en-1-yl>-2H-pyran-2-one 
• 168416-26-0 C₁₄⁽¹³⁾CH₂₁⁽²⁾H₃O₂ 
• 168416-23-7 <(R,S)-6-<13CD3>>-2,6,6-trimethylcyclohexyl p-toluenesulfonyl hydrazone 

Relevant academic research and scientific papers

Synthesis of 1-[13CD3]-9-cis-retinoic acid

1-[13CD3]-9-cis-Retinoic acid was prepared in 8 steps from 2,6-dimethylcyclohexanone. Alkylation of 2,6-dimethylcyclohexanone under LiHMDS/MnBr2/13CD3I gave the corresponding labeled 2-[13CD3]-2,2,6-trimethylcyclohexanone 4 in good yield. Further functionalization of 4 to 6-[13CD3]-β-cyclocitral 6 proceeded through a Shapiro reaction. Aldehyde 6 was condensed with ethyl 3,3-dimethylacrylate to afford the corresponding bicyclic pyranone 7. Reduction of 7 to lactol 8, followed by acid-catalyzed ring opening gave the 9-cis-aldehyde 9. Wittig-Horner olefination and saponification afforded the title compound in good overall yield and in excellent isotopic purity.