2. Academic Validation
  3. First Total Synthesis, Structure Revision, and Natural History of the Smallest Cytochalasin: (+)-Periconiasin G

First Total Synthesis, Structure Revision, and Natural History of the Smallest Cytochalasin: (+)-Periconiasin G

  • Chemistry. 2016 Oct 17;22(43):15257-15260. doi: 10.1002/chem.201603734.
Mehdi Zaghouani 1,  Caroline Kunz 1 2,  Laura Guédon 1,  Florent Blanchard 3,  Bastien Nay 4
Affiliations

Affiliations

  • 1 Muséum National d'Histoire Naturelle, CNRS (UMR 7245), Sorbonne Universités, 57 rue Cuvier (CP 54), 75005, Paris, France.
  • 2 Sorbonne Universités, Université Pierre et Marie Curie, Paris 6, UFR 927, Paris, France.
  • 3 Institut de Chimie des Substances Naturelles (ICSN-CNRS), 1 Avenue de la Terrasse, 91198, Gif-sur-Yvette Cedex, France.
  • 4 Muséum National d'Histoire Naturelle, CNRS (UMR 7245), Sorbonne Universités, 57 rue Cuvier (CP 54), 75005, Paris, France. bnay@mnhn.fr.
PMID: 27556729 DOI: 10.1002/chem.201603734
Abstract

The total synthesis of the smallest cytochalasin isolated so far, periconiasin G, which bears a seven-membered ring in lieu of the usual macrocycle, has been performed from both enantiomers of citronellal, relying on an intramolecular Diels-Alder reaction in favor of the natural endo stereochemistry. We show that, among the four synthesized stereoisomers, including the exo isomers, the one matching the NMR data of the natural product was not that assigned in the original report, imposing structure revision. The natural product, previously isolated from a plant-mutualistic fungus, was biologically investigated taking into account its natural history, showing significant effects against the phytopathogenic fungus Botrytis cinerea and thus opening new opportunities in combating this pest.

Keywords

antifungal activities; cytochalasin; periconiasin; structure revision; total synthesis.

Figures
Products