An approach to the tricyclic core of madangamines based upon a biogenetic scheme.
[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.
Tong
Han Min
HM
Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
Martin
Marie-Thérèse
MT
Chiaroni
Angèle
A
Bénéchie
Michel
M
Marazano
Christian
C
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
D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; C508399:madangamine A