title: An approach to the tricyclic core of madangamines based upon a biogenetic scheme.
abstract: [reaction: see text] A short synthesis of intermediates possessing the tricyclic core of natural madangamines, bioactive alkaloids found in marine sponges, is described. The key reaction entails the condensation of the sodium salt of diethylacetonedicarboxylate with a dihydropyridinium salt derivative. This new approach is modeled on a biogenetic proposal linking madangamines to ircinals, related alkaloids occurring in sponges of the same order.
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
authors.forename: Han Min
authors.initials: HM
authors.lastname: Tong
authors.forename: Marie-Thérèse
authors.initials: MT
authors.lastname: Martin
authors.forename: Angèle
authors.initials: A
authors.lastname: Chiaroni
authors.forename: Michel
authors.initials: M
authors.lastname: Bénéchie
authors.forename: Christian
authors.initials: C
authors.lastname: Marazano
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D000818:Animals; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry
chemical_list: D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; C508399:madangamine A