Journal of labelled compounds and radiopharmaceuticals p. 755 - 763 (1995)
Update date:2022-08-04
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Bennani
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.
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