title: A concise synthesis of turneforcidine via a metalloiminium ion cyclization terminated by the 2-(methylthio)-3-(trimethylsilyl)-1-propenyl moiety.
abstract: A concise synthetic route to racemic turneforcidine (1) is described that relies on the stereocontrolled cyclization of the 2-(methylthio)-3-(trimethylsilyl)-1-propenyl bearing imine 5 in the presence of TiCl(4). Reaction: see text.
authors.affiliation: Department of Chemistry and Biochemistry, Montana State University, Bozeman, MT 59717, USA.
authors.forename: D K
authors.initials: DK
authors.lastname: An
authors.forename: D
authors.initials: D
authors.lastname: Duncan
authors.forename: T
authors.initials: T
authors.lastname: Livinghouse
authors.forename: P
authors.initials: P
authors.lastname: Reid
mesh_terms: D007097:Imines / Q000737:chemistry; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis*; D014025:Titanium / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis
chemical_list: C433404:2-(thiomethyl)-3-trimethylsilyl-1-propenyl; D007097:Imines; D011763:Pyrrolizidine Alkaloids; D014297:Trimethylsilyl Compounds; C443726:turneforcidine; C025096:titanium tetrachloride; D014025:Titanium