title: Synthesis of (+)-zerumin B using a regioselective singlet oxygen furan oxidation.
abstract: A short and efficient synthesis of the antitumor diterpenoid (+)-zerumin B has been accomplished starting from (+)-sclareolide. At the heart of the synthetic strategy lies the regioselective formation of the alpha-substituted gamma-hydroxybutenolide moiety of zerumin B. This was achieved by means of a [1,4] O-->C triisopropylsilyl migration followed by singlet oxygen (1 O 2) oxidation of the resulting 2-triisopropylsilyl-3-(alpha-hydroxy)alkylfuran.
authors.affiliation: Department of Chemistry, University of Crete, Vasilika Vouton, 71003 Iraklion, Crete, Greece.
authors.forename: Ioannis
authors.initials: I
authors.lastname: Margaros
authors.forename: Georgios
authors.initials: G
authors.lastname: Vassilikogiannakis
mesh_terms: D004224:Diterpenes / Q000138:chemical synthesis*; D005663:Furans / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D026082:Singlet Oxygen / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; D005663:Furans; D007783:Lactones; C520384:zerumin B; D026082:Singlet Oxygen; C039281:furan