title: Synthesis of (-)-epibatidine.
abstract: The synthesis of (-)-epibatidine has been accomplished utilizing a highly exo-selective asymmetric hetero Diels-Alder reaction. The key steps employed to transform the resulting bicycle into the natural product include a fluoride-promoted fragmentation and a Hofmann rearrangement. Reaction: see text.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. evans@chemistry.harvard.edu
authors.forename: D A
authors.initials: DA
authors.lastname: Evans
authors.forename: K A
authors.initials: KA
authors.lastname: Scheidt
authors.forename: C W
authors.initials: CW
authors.lastname: Downey
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D018712:Analgesics, Non-Narcotic / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D018722:Nicotinic Agonists / Q000138:chemical synthesis / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D011898:Ranidae; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D018712:Analgesics, Non-Narcotic; D019086:Bridged Bicyclo Compounds, Heterocyclic; D018722:Nicotinic Agonists; D011725:Pyridines; C082748:epibatidine