title: Semisynthesis of the antiviral abietane diterpenoid jiadifenoic acid C from callitrisic acid (4-epidehydroabietic acid) isolated from sandarac resin.
abstract: 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.
authors.affiliation: Departamento de Química Orgánica, Universidad de Valencia , Dr. Moliner 50, 46100 Burjassot, Valencia, Spain.
authors.forename: Miguel A
authors.initials: MA
authors.lastname: González
authors.forename: Ramón J
authors.initials: RJ
authors.lastname: Zaragozá
mesh_terms: D045784:Abietanes / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D029822:Enterovirus B, Human / Q000187:drug effects*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D012116:Resins, Plant / Q000737:chemistry*
chemical_list: D045784:Abietanes; D000998:Antiviral Agents; D012116:Resins, Plant; C000594632:epidehydroabietic acid; C000594631:jiadifenoic acid C