Modification of the intact retinoid structure in the cyclohexenyl region: Alkylation of methyl 4-oxoretinoate

Article abstract of DOI:10.1055/s-1993-26008

Alkylation of methyl 4-oxoretinoate under kinetic-control conditions gives predominantly 3-alkyl-4-oxoretinoates. 3,3-Disubstituted 4-oxoretinoates are obtained similarly from the 3-monosubstituted derivatives, although introduction of the second substituent is more difficult. Evidence has been obtained for a much slower rate of alkylation α to the ester group.