6533b85dfe1ef96bd12bf209

RESEARCH PRODUCT

Semisynthesis of the Antiviral Abietane Diterpenoid Jiadifenoic Acid C from Callitrisic Acid (4-Epidehydroabietic Acid) Isolated from Sandarac Resin

Ramón J. ZaragozáMiguel A. González

subject

PharmacologyAllylic rearrangementNatural productMolecular StructureChemistryOrganic ChemistrySandaracPharmaceutical ScienceRegioselectivityAntiviral AgentsSemisynthesisTerpenoidEnterovirus B HumanAnalytical Chemistrychemistry.chemical_compoundComplementary and alternative medicineAbietanesDrug DiscoveryMolecular MedicineOrganic chemistryNuclear Magnetic Resonance BiomolecularOxidation-ReductionResins PlantIsopropylAbietane

description

The semisynthesis of the antiviral abietane diterpenoid (+)-jiadifenoic acid C starting from the available methyl ester of callitrisic acid (4-epidehydroabietic acid) isolated from sandarac resin is reported. A protocol for the isolation of methyl callitrisate (methyl 4-epidehydroabietate) in gram quantities from sandarac resin is also described. Allylic C-17 oxygenation was introduced by regioselective dehydrogenation of the isopropyl group of methyl callitrisate with DDQ followed by selenium-catalyzed allylic oxidation. Ester hydrolysis afforded (+)-jiadifenoic acid C in 22% overall yield from methyl callitrisate. This semisynthetic route provides a convenient source of this anti-Coxsackie virus B natural product for further biological studies.

yearjournalcountryeditionlanguage
2014-08-29Journal of Natural Products
https://doi.org/10.1021/np500569y