title: Total synthesis of (+)-epiquinamide.
abstract: The stereoselective total synthesis of the novel quinolizidine alkaloid (+)-epiquinamide is presented, starting from the amino acid l-allysine ethylene acetal. Key steps in the synthesis involved a highly diastereoselective N-acyliminium ion allylation and a ring-closing metathesis reaction to provide the bicyclic skeleton. [reaction: see text]
authors.affiliation: Chiralix B.V., P.O. Box 31070, 6503 CB Nijmegen, The Netherlands, Radboud University Nijmegen, IMM, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands.
authors.forename: Marloes A
authors.initials: MA
authors.lastname: Wijdeven
authors.forename: Peter N M
authors.initials: PN
authors.lastname: Botman
authors.forename: Roel
authors.initials: R
authors.lastname: Wijtmans
authors.forename: Hans E
authors.initials: HE
authors.lastname: Schoemaker
authors.forename: Floris P J T
authors.initials: FP
authors.lastname: Rutjes
authors.forename: Richard H
authors.initials: RH
authors.lastname: Blaauw
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D008968:Molecular Conformation; D015394:Molecular Structure; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D011807:Quinolizines; C481035:epiquinamide