Davis Oxidation

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The Experts below are selected from a list of 567 Experts worldwide ranked by ideXlab platform

Lixiong Zhang - One of the best experts on this subject based on the ideXlab platform.

Shengfeng Zhou - One of the best experts on this subject based on the ideXlab platform.

Runyu Zhu - One of the best experts on this subject based on the ideXlab platform.

Liang Huang - One of the best experts on this subject based on the ideXlab platform.

  • Novel Concise Synthesis of (−)-Clausenamide
    Chinese Journal of Chemistry, 2013
    Co-Authors: Di Liu, Liang Huang
    Abstract:

    A six-step synthesis of (−)-clausenamide is described. Optically pure (R,E)-1,3-diphenylallylic alcohol was acetylated and then subjected to an Ireland-Claisen rearrangement, giving the γ,δ-unsaturated acid, which underwent a substrate-induced stereoselective bromolactonization to afford the expected all-equatorial substituted bromo-δ-lactone. An unusual chemo-selective aminolysis of the lactone resulted in the formation of a γ,δ-epoxy-amide in stereospecific manner. Base-promoted cyclization of this intermediate and the subsequent Davis Oxidation furnished the synthesis, delivering the final product in >99% ee and up to 34% overall yield.

Di Liu - One of the best experts on this subject based on the ideXlab platform.

  • Novel Concise Synthesis of (−)-Clausenamide
    Chinese Journal of Chemistry, 2013
    Co-Authors: Di Liu, Liang Huang
    Abstract:

    A six-step synthesis of (−)-clausenamide is described. Optically pure (R,E)-1,3-diphenylallylic alcohol was acetylated and then subjected to an Ireland-Claisen rearrangement, giving the γ,δ-unsaturated acid, which underwent a substrate-induced stereoselective bromolactonization to afford the expected all-equatorial substituted bromo-δ-lactone. An unusual chemo-selective aminolysis of the lactone resulted in the formation of a γ,δ-epoxy-amide in stereospecific manner. Base-promoted cyclization of this intermediate and the subsequent Davis Oxidation furnished the synthesis, delivering the final product in >99% ee and up to 34% overall yield.