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RESEARCH PRODUCT
Synthesis of fluorinated drimanes. Preparation of 9αF-drimenin
David PardoAna C. CuñatAntonio AbadConsuelo Agullósubject
Allylic rearrangementBicyclic moleculeStereochemistryOrganic ChemistryElectrophilic fluorinationHalogenationSesquiterpeneBiochemistrychemistry.chemical_compoundchemistryDrug DiscoveryWittig reactionOrganic chemistryStereoselectivitydescription
Abstract A stereoselective approach to the 9α-fluorinated analogue of the natural drimane sesquiterpene drimenin starting from β-ionone is described. β-Ionone is transformed into a bicyclic β-cetoester from which 9αF-drimenin is prepared through stereoselective electrophilic fluorination at the C-9 with N -fluorobenzenesulfonimide followed by Wittig methylenation, allylic bromination, bromine-hydroxyl exchange and γ-lactonization.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2003-02-01 | Tetrahedron Letters |