Part I: Stereoselective syntheses of (+)-perovskone and (+)-salvadione-A / Part II: Total synthesis of (±)-komaroviquinone and studies toward the synthesis of (+)-komaroviquinone / Part III: The regiochemistry of the ortho-Claisen rearrangement of bis-(
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In Part I, the total syntheses of (+)-perovskone and (+)-salvadione-A were achieved using optically active p-benzoquinone as a common intermediate in the Diels-Alder reactions. In Part II, the total synthesis of (±)-komaroviquinone has been achieved. An efficient Friedel-Crafts cycloalkylation method was developed in the study toward the stereoselective synthesis of (+)-komaroviquinone. In Part III, the ortho-Claisen rearrangement of the bis-allyloxy ethers of naphthalene, anthracene, phenanthrene and heterocycle derivatives were studied. Every reaction gave only a single rearranged product, even where two or three isomers were possible. In Part IV, a mild and efficient epoxidation of electron rich olefins was developed, applying β-Bromo dimethylalkoxysulfonium ion as the common intermediate.