6533b7dcfe1ef96bd12731d6

RESEARCH PRODUCT

ChemInform Abstract: Trienediolates of Hexadienoic Acids in Synthesis. Synthesis of Retinoic and nor-Retinoic Acids.

Ramon MestresA. TortajadaJosé E. ClarMaría José AurellIsmael CarneSalvador GilMargarita Parra

subject

chemistry.chemical_compoundAddition reactionDeprotonationchemistryRetinoic acidchemistry.chemical_elementLithiumGeneral MedicineSorbic acidMedicinal chemistry

description

Abstract Double deprotonation of either (E,E)-3-methyl-2,4-hexadienoic acid 2, or 4,6-dimethyldihydro-2-pyrone 3 generates apparently the same lithium trienediolate, which affords ω-hydroxy acids 9 on reaction with ketones 7. Hydroxy acids 9 are easily dehydrated to octatrienoic acids 5, which are structurally related to retinoic acid. Similarly, sorbic acid 1 leads to nor-retinoic acid analogs 6.

https://doi.org/10.1002/chin.199345296