title: Total synthesis of the purported structure of sclerophytin F.
abstract: The synthesis of the compound that has been proposed to be the natural product sclerophytin F has been completed from a known vinylogous carbonate. The synthetic strategy relied upon rearrangement of a catalytically generated ylide-like intermediate to produce an oxabicyclo[6.2.1]-5-undecen-9-one and an intermolecular Diels-Alder reaction to construct the complete tricyclic core found in the natural product. Comparison of the spectroscopic data for synthetic material to that reported for sclerophytin F shows that the natural product does not have the revised structure possessing the 3S configuration (*) proposed previously.
authors: WestCHEM, School of Chemistry, Joseph Black Building, University of Glasgow , University Avenue, Glasgow, G12 8QQ, United Kingdom.
authors: J Stephen
authors: JS
authors: Clark
authors: Laetitia
authors: L
authors: Delion
authors: Louis J
authors: LJ
authors: Farrugia
mesh_terms: D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001952:Bridged-Ring Compounds; D005663:Furans; C451080:sclerophytin F