Synthesis of the 4-oxygenated retinoid metabolites.
The efficient synthesis of 4-hydroxylated metabolites of various retinoids is described. Allylic bromination of beta-ionone, retinal, and methyl retinoate followed by treatment with aqueous AcOH and saponification afforded the 4-hydroxy analogues in 64-79% yields. With the conjugated polyenes, retinal and methyl retinoate, about 25% of the products were found to be the 13-cis isomers. Purification of isomer mixtures by HPLC permitted stereochemical assignments after 1H NMR analysis.
D055598:Chemical Phenomena; D002621:Chemistry; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D012176:Retinoids / Q000138:chemical synthesis* / Q000378:metabolism; D013056:Spectrophotometry, Ultraviolet
D012176:Retinoids