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  • total synthesis of ingenol
    Journal of the American Chemical Society, 2003
    Co-Authors: Andrew Nickel, Toru Maruyama, Haifeng Tang, Prescott D Murphy, Blake Greene, Naeem Yusuff, John L Wood
    Abstract:

    Total synthesis of ingenol, a diterpene isolated from the genus Euphorbia, was accomplished on the basis of the novel key Reactions. The highly strained ingenane skeleton was constructed through an intramolecular cyclization Reaction of an acetylene dicobalt complex followed by a Rearrangement Reaction of an epoxy alcohol. The C(3),C(4),C(5)-triol moiety was introduced by a stereoselective double dihydroxylation Reaction of a diene having C(2)−C(3) and C(4)−C(5) double bonds.