title: Enantioselective synthesis of (-)-dendroprimine and isomers.
abstract: An enantioselective and diastereoselective synthesis of six 5,7-dimethylindolizidine isomers is described via an intramolecular cyclization that involves an allylsilyl nucleophilic group and an acyliminium ion. The first total synthesis of naturally occurring (-)-dendroprimine has been achieved in five steps.
authors.affiliation: Département de Chimie, UMR 6504, CNRS et Université Blaise Pascal (Clermont-Ferrand), 63177 Aubière, France.
authors.forename: Axelle
authors.initials: A
authors.lastname: De Saboulin Bollena
authors.forename: Yvonne
authors.initials: Y
authors.lastname: Gelas-Mialhe
authors.forename: Jean-Claude
authors.initials: JC
authors.lastname: Gramain
authors.forename: Anne
authors.initials: A
authors.lastname: Perret
authors.forename: Roland
authors.initials: R
authors.lastname: Remuson
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D003500:Cyclization; D031667:Dendrobium / Q000737:chemistry; D006865:Hydrogenation; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D007212:Indolizines; C488243:dendroprimine