title: Application of a Raney-cobalt-mediated tandem reductive cyclization protocol to total syntheses of the Aspidosperma alkaloids (±)-limaspermidine and (±)-1-acetylaspidoalbidine.
abstract: The racemic modification of the Aspidosperma alkaloid limaspermidine (1) has been prepared in ten steps including one involving a Raney-cobalt-mediated tandem reductive cyclization of nitrile 8 to give the tetracyclic system 9b. Compound (±)-1 has been converted over two steps into (±)-1-acetylaspidoalbidine [(±)-13].
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra ACT 0200, Australia.
authors.forename: Shen H
authors.initials: SH
authors.lastname: Tan
authors.forename: Martin G
authors.initials: MG
authors.lastname: Banwell
authors.forename: Anthony C
authors.initials: AC
authors.lastname: Willis
authors.forename: Tristan A
authors.initials: TA
authors.lastname: Reekie
mesh_terms: D030009:Aspidosperma / Q000737:chemistry*; D002227:Carbazoles; D002625:Chemistry, Organic / Q000379:methods*; D003035:Cobalt / Q000737:chemistry*; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry; D024301:Plant Bark / Q000737:chemistry; D013237:Stereoisomerism; D014687:Venezuela
chemical_list: C549511:1-acetylaspidoalbidine; D002227:Carbazoles; D026121:Indole Alkaloids; D009570:Nitriles; C579383:limaspermidine; C041514:carbazole; D003035:Cobalt