Synthesis of (+)-zerumin B using a regioselective singlet oxygen furan oxidation
(Chemical Equation Presented) 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 α-substituted γ-hydroxybutenolide moiety of zerumin B. This was achieved by means of a [1,4] O→C triisopropylsilyl migration followed by singlet oxygen (1O2) oxidation of the resulting 2-triisopropylsilyl-3-(α-hydroxy)alkylfuran.
Margaros, Ioannis,Vassilikogiannakis, Georgios
p. 2021 - 2023
(2008/09/21)
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