title: A short, organocatalytic formal synthesis of (-)-swainsonine and related alkaloids.
abstract: A short synthesis of hydroxyalkyl dihydropyrroles has been developed that involves the coupling of propargylamines with α-chloroaldehydes, followed by Lindlar reduction and a one-pot epoxide formation/opening sequence. The application of this process to the synthesis of unnatural iminosugars and a formal synthesis of (-)-swainsonine is described.
authors.affiliation: Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada.
authors.forename: Vijay
authors.initials: V
authors.lastname: Dhand
authors.forename: Jason A
authors.initials: JA
authors.lastname: Draper
authors.forename: Jarod
authors.initials: J
authors.lastname: Moore
authors.forename: Robert
authors.initials: R
authors.lastname: Britton
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D017026:Swainsonine / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000470:Alkaloids; D004852:Epoxy Compounds; D017026:Swainsonine