title: Chiroptical study and absolute configuration of securinine oxidation products.
abstract: Time-dependant density functional theory-electronic circular dichroism spectra prediction was carried out to study the absolute configuration of phyllanthidine-type derivatives 5 and 6, derived from securinine (1) and its enantiomer virosecurinine (2), respectively. This method demonstrated to be very reliable in this alkaloid series. Thus, 5 and 6 shared the same stereochemistry as their parent precursors, confirming the retentive nature of the oxidation sequence. In addition, this study highlighted the key role of the methylene bridge (BC ring) in the chiroptical activity of these compounds. These results fully clarified the stereochemical relationships between the phyllanthidine and the securinine subgroups.
authors: a Laboratoire de Pharmacognosie UMR CNRS 8638 COMETE, Faculté de Pharmacie, Université Paris Descartes , 4 Avenue de l'Observatoire, F-75006 Paris , France.
authors: Egor
authors: E
authors: Chirkin
authors: William
authors: W
authors: Atkatlian
authors: Quyên
authors: Q
authors: Do
authors: Thomas
authors: T
authors: Gaslonde
authors: Thi-Hanh
authors: TH
authors: Dufat
authors: Sylvie
authors: S
authors: Michel
authors: Pascale
authors: P
authors: Lemoine
authors: Grégory
authors: G
authors: Genta-Jouve
authors: François-Hugues
authors: FH
authors: Porée
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D001381:Azepines / Q000737:chemistry*; D002942:Circular Dichroism; D019665:Euphorbiaceae / Q000737:chemistry; D006572:Heterocyclic Compounds, Bridged-Ring / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010880:Piperidines / Q000737:chemistry*; D035261:Plant Components, Aerial / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001381:Azepines; D006572:Heterocyclic Compounds, Bridged-Ring; D007783:Lactones; D010880:Piperidines; C012607:virosecurinine; C000785:securinine
keywords: TDDFT-ECD; X-ray crystallography; absolute configuration; phyllanthidine; securinine