6533b830fe1ef96bd1296fab
RESEARCH PRODUCT
Trienediolates of hexadienoic acids in synthesis. synthesis of retinoic and nor-retinoic acids.
Ramon MestresJosé E. ClarA. TortajadaMaría José AurellSalvador GilMargarita ParraIsmael Carnesubject
chemistry.chemical_classificationAddition reactionKetoneChemistryOrganic ChemistryRetinoic acidBiochemistrychemistry.chemical_compoundDeprotonationDrug DiscoveryOrganic chemistryStereoselectivityAliphatic compoundSorbic acidAcetophenonedescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1993-07-01 | Tetrahedron |