Synthesis of (+)-zerumin B using a regioselective singlet oxygen furan oxidation.
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.
Margaros
Ioannis
I
Department of Chemistry, University of Crete, Vasilika Vouton, 71003 Iraklion, Crete, Greece.
Vassilikogiannakis
Georgios
G
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
D004224:Diterpenes; D005663:Furans; D007783:Lactones; C520384:zerumin B; D026082:Singlet Oxygen; C039281:furan