An approach to the tricyclic core of madangamines based upon a biogenetic scheme

Org Lett. 2005 Jun 9;7(12):2437-40. doi: 10.1021/ol050740i.

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.

MeSH terms

  • Alkaloids / chemical synthesis*
  • Animals
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Porifera / chemistry

Substances

  • Alkaloids
  • Heterocyclic Compounds, 4 or More Rings
  • madangamine A