6533b836fe1ef96bd12a0737
RESEARCH PRODUCT
Trienediolates of hexadienoic acids in synthesis. Addition to unsaturated ketones. A convergent approach to the synthesis of retinoic acids
Luisa CeitaMaría José AurellRamon MestresMargarita ParraA. Tortajadasubject
ArylOrganic Chemistrychemistry.chemical_elementRegioselectivitymedicine.diseaseBiochemistrychemistry.chemical_compoundDeprotonationchemistryAcid catalyzedUnsaturated ketoneDrug DiscoverymedicineOrganic chemistryLithiumDehydrationCarbondescription
Abstract The regioselectivity of the addition of the lithium trienediolates generated from hexa-2,4dienoic acids 1 and 2 or the dihydropyran-2ones 4 and 5 to unsaturated ketones 6 is studied. Equilibration conditions favour reaction of the trienediolates through their ω carbon, and the ketones according to 1,2- and 1,4-additions. β-Ionone 6a and the aryl-butenone 6b lead to the 1,2-ω-adducts 8 , which undergo a facile acid catalyzed dehydration to retmoic acids 11 . On reaction with the unsaturated ketone 6b or with the aryl ketones 21 , the trimethyldihydropyran-2one S leads to γ-adducts derived from deprotonation of the chain methyl mbstituent along with the 1,4-ω-adducts.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1995-03-01 | Tetrahedron |