title: Chemoenzymatic formal synthesis of (-)- and (+)-epibatidine.
abstract: The cis-dihydrocatechol, derived from enzymatic cis-dihydroxylation of bromobenzene using the microorganism Pseudomonas putida UV4, was converted into (-)-epibatidine in eleven steps with complete stereocontrol. In addition, an unprecedented palladium-catalysed disproportionation reaction gave the (+)-enantiomer of an advanced key intermediate employed in a previous synthesis of epibatidine.
authors.affiliation: School of Chemistry and Chemical Engineering, Queen's University, Belfast BT9 5AG, UK.
authors.forename: Derek R
authors.initials: DR
authors.lastname: Boyd
authors.forename: Narain D
authors.initials: ND
authors.lastname: Sharma
authors.forename: Magdalena
authors.initials: M
authors.lastname: Kaik
authors.forename: Peter B A
authors.initials: PB
authors.lastname: McIntyre
authors.forename: Paul J
authors.initials: PJ
authors.lastname: Stevenson
authors.forename: Christopher C R
authors.initials: CC
authors.lastname: Allen
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000378:metabolism; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D016958:Pseudomonas putida / Q000201:enzymology*; D011725:Pyridines / Q000138:chemical synthesis* / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D011725:Pyridines; D010165:Palladium; C082748:epibatidine