title: Viability of a [2 + 2 + 1] Hetero-Pauson-Khand Cycloaddition Strategy toward Securinega Alkaloids: Synthesis of the BCD-Ring Core of Securinine and Related Alkaloids.
abstract: Preliminary results related to the development of [2 + 2 + 1]-oxa-hetero-Pauson-Khand cycloaddition strategy toward the Securinega alkaloids are reported. The critical tricyclic BCD-ring core was assembled in only nine linear steps from cheap 4-hydroxy-l-proline. The study provides valuable insight into the scope of a rare hetero-Pauson-Khand reaction, a powerful tool for the rapid construction of butenolide-containing natural products.
authors.affiliation: Laboratoire de Pharmacognosie UMR CNRS 8638, Faculté de Pharmacie, Université Paris Descartes, 4 Avenue de l'Observatoire, F-75006 Paris, France.
authors.forename: Egor
authors.initials: E
authors.lastname: Chirkin
authors.affiliation: Laboratoire de Pharmacognosie UMR CNRS 8638, Faculté de Pharmacie, Université Paris Descartes, 4 Avenue de l'Observatoire, F-75006 Paris, France.
authors.forename: Sylvie
authors.initials: S
authors.lastname: Michel
authors.affiliation: Laboratoire de Pharmacognosie UMR CNRS 8638, Faculté de Pharmacie, Université Paris Descartes, 4 Avenue de l'Observatoire, F-75006 Paris, France.
authors.forename: François-Hugues
authors.initials: FH
authors.lastname: Porée
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D061565:Cycloaddition Reaction; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006572:Heterocyclic Compounds, Bridged-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D006909:Hydroxyproline / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000470:Alkaloids; D001381:Azepines; D001688:Biological Products; D006571:Heterocyclic Compounds; D006572:Heterocyclic Compounds, Bridged-Ring; D007783:Lactones; D010880:Piperidines; C000785:securinine; D006909:Hydroxyproline