title: Enantioselective synthesis of nicotinic receptor probe 7,8-difluoro-1,2,3,4,5,6- hexahydro-1,5-methano-3-benzazocine.
abstract: [Structure: see text] The development of a concise enantioselective synthesis of nicotinic alkaloid 1 is presented. The route features the synthesis and use of a "stable" aliphatic triflate 21 in an alkylation step to generate Heck precursor 24 and an enantioselective cyclization to establish a compound with the key [3.2.1]-bicyclic core, 29.
authors.affiliation: Pfizer Global Research and Development, Groton Laboratories, Pfizer Inc., Groton, Connecticut 06340, USA.
authors.forename: Crystal G
authors.initials: CG
authors.lastname: Bashore
authors.forename: Michael G
authors.initials: MG
authors.lastname: Vetelino
authors.forename: Michael C
authors.initials: MC
authors.lastname: Wirtz
authors.forename: Paige R
authors.initials: PR
authors.lastname: Brooks
authors.forename: Heather N
authors.initials: HN
authors.lastname: Frost
authors.forename: Ruth E
authors.initials: RE
authors.lastname: McDermott
authors.forename: David C
authors.initials: DC
authors.lastname: Whritenour
authors.forename: John A
authors.initials: JA
authors.lastname: Ragan
authors.forename: Jennifer L
authors.initials: JL
authors.lastname: Rutherford
authors.forename: Teresa W
authors.initials: TW
authors.lastname: Makowski
authors.forename: Steven J
authors.initials: SJ
authors.lastname: Brenek
authors.forename: Jotham W
authors.initials: JW
authors.lastname: Coe
mesh_terms: D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015335:Molecular Probes; D009538:Nicotine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D011978:Receptors, Nicotinic / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C522876:7,8-difluoro-1,2,3,4,5,6- hexahydro-1,5-methano-3-benzazocine; D015335:Molecular Probes; D011978:Receptors, Nicotinic; D009538:Nicotine