title: Total synthesis of the putative structure of stemonidine: the definitive proof of misassignment.
abstract: [structure: see text] The total synthesis of the putative structure of the Stemona alkaloid stemonidine has been completed. The key transformations include a 1,3-dipolar cycloaddition of a chiral nitrone derived from (S)-prolinol and a spirolactonization process involving the generation of the critical stereocenter. The NMR data of the synthetic material do not match those reported for the natural product. It is concluded that the structure assigned to stemonidine is incorrect, and it must be reassigned as stemospironine.
authors.affiliation: Universitat Autonoma de Barcelona, Departament de Química, 08193 Bellaterra, Spain.
authors.forename: Francisco
authors.initials: F
authors.lastname: Sánchez-Izquierdo
authors.forename: Pilar
authors.initials: P
authors.lastname: Blanco
authors.forename: Félix
authors.initials: F
authors.lastname: Busqué
authors.forename: Ramón
authors.initials: R
authors.lastname: Alibés
authors.forename: Pedro
authors.initials: P
authors.lastname: de March
authors.forename: Marta
authors.initials: M
authors.lastname: Figueredo
authors.forename: Josep
authors.initials: J
authors.lastname: Font
authors.forename: Teodor
authors.initials: T
authors.lastname: Parella
mesh_terms: D000470:Alkaloids / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry; D006573:Heterocyclic Compounds, 1-Ring / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry; D009930:Organic Chemicals / Q000138:chemical synthesis* / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000470:Alkaloids; D001372:Aza Compounds; D006573:Heterocyclic Compounds, 1-Ring; D007783:Lactones; D009589:Nitrogen Oxides; D009930:Organic Chemicals; D011759:Pyrrolidines; D013141:Spiro Compounds; C015388:nitrones; C520152:stemonidine; C010509:prolinol