Approaches toward the total synthesis of the nine-membered thio-lactone core of griseoviridin.
Three different approaches toward the synthesis of the macrocyclic thiolactone core of griseoviridin have been studied. Intramolecular palladium-catalyzed thiol coupling and esterification (carboxylate activation) have led to the formation of unexpected rearranged products. An intermolecular palladium-catalyzed thiol/vinyl iodide coupling followed by an esterification (alcohol activation) ultimately led to the nine-membered core of griseoviridin.
Moreau
Xavier
X
Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse 91198, France.
Campagne
Jean-Marc
JM
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004951:Esterification; D007783:Lactones / Q000138:chemical synthesis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis*; D013302:Streptomyces / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis
D000900:Anti-Bacterial Agents; D007783:Lactones; D010455:Peptides; D013438:Sulfhydryl Compounds; D010165:Palladium; C010583:griseoviridin