title: Synthesis of a dicyano abietane, a key intermediate for the anti-inflammatory agent TBE-31.
abstract: The synthesis of dicyano abietane 11, a potential precursor to the biologically active tricyclic bis-cyano enone 6 (TBE-31), was accomplished in eight steps from epoxide 13. The synthesis features a Lewis acid promoted stereoselective cyclization of epoxide 13 to generate the tricyclic ring system 12 in one step.
authors.affiliation: Department of Chemistry, Dartmouth College , Hanover, New Hampshire 03755, United States.
authors.forename: Evans O
authors.initials: EO
authors.lastname: Onyango
authors.forename: Liangfeng
authors.initials: L
authors.lastname: Fu
authors.forename: Gordon W
authors.initials: GW
authors.lastname: Gribble
mesh_terms: D045784:Abietanes / Q000138:chemical synthesis* / Q000737:chemistry; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D008968:Molecular Conformation; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D045784:Abietanes; D000894:Anti-Inflammatory Agents, Non-Steroidal; D009570:Nitriles; D010616:Phenanthrenes; C531972:TBE 31