title: Synthesis of four diastereomers of sclerophytin F and structural reassignment of several sclerophytin natural products.
abstract: Synthesis of the triol that has been proposed to be the marine natural product sclerophytin F has been completed along with the syntheses of three diastereomers. Comparison of the NMR spectroscopic data for all four compounds to the data reported for the natural product reveals that sclerophytin F is not the 3S diastereomer of sclerophytin A as proposed by Friedrich and Paquette. Re-analysis of the NMR spectroscopic data for known sclerophytin natural products and synthetic analogues leads to the conclusion that sclerophytins E and F are the same compound. This finding has allowed structural reassignment of several other cladiellin natural products.
authors: WestCHEM, School of Chemistry, Joseph Black Building, University of Glasgow, University Avenue, Glasgow G12 8QQ (UK). stephen.clark@glasgow.ac.uk.
authors: J Stephen
authors: JS
authors: Clark
authors: Laëtitia
authors: L
authors: Delion
authors: Louis J
authors: LJ
authors: Farrugia
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry*; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008670:Metals / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D001952:Bridged-Ring Compounds; D005663:Furans; D007659:Ketones; D008670:Metals; C451079:sclerophytin E; C451080:sclerophytin F
keywords: carbenoids; natural products; rearrangement; structure elucidation; total synthesis