title: Asymmetric synthesis of the tropane alkaloid (+)-pseudococaine via ring-closing iodoamination.
abstract: Ring-closing iodoamination of tert-butyl 2-hydroxy-7-[N-methyl-N-(α-methyl-p-methoxybenzyl)amino]cyclohept-3-ene-1-carboxylates proceeds with concomitant loss of the N-α-methyl-p-methoxybenzyl group to give the corresponding 8-azabicyclo[3.2.1]octane scaffolds in >99:1 dr. Subsequent elaboration of one of these templates provided access to (+)-pseudococaine hydrochloride, in seven steps and 31% overall yield from commercially available starting materials.
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.
authors.forename: E Anne
authors.initials: EA
authors.lastname: Brock
authors.forename: Stephen G
authors.initials: SG
authors.lastname: Davies
authors.forename: James A
authors.initials: JA
authors.lastname: Lee
authors.forename: Paul M
authors.initials: PM
authors.lastname: Roberts
authors.forename: James E
authors.initials: JE
authors.lastname: Thomson
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry; D003042:Cocaine / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014326:Tropanes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D002264:Carboxylic Acids; D014326:Tropanes; C016084:pseudococaine; D003042:Cocaine