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Synthesis 1993; 1993(11): 1095-1098
DOI: 10.1055/s-1993-26008
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Modification of the Intact Retinoid Structure in the Cyclohexenyl Region: Alkylation of Methyl 4-Oxoretinoate

Y. Fulmer Shealy* , Carla A. Hosmer, James M. Riordan
  • *Southern Research Institute, 2000 Ninth Avenue, South Birmingham, Alabama 35255-5305, USA
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Publication Date:
29 April 2002 (online)

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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.