Boronic Acid-Catalyzed Final-Stage Site-Selective Acylation for the Total Syntheses of O-3'-Acyl Bisabolol β-D-Fucopyranoside Natural Products and Their Analogues

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  • Nakamura Yuki
    Laboratory of Organic Chemistry for Drug Development and Research Laboratories, Department of Pharmaceutical Sciences, Kitasato University
  • Ochiai Takayuki
    Laboratory of Organic Chemistry for Drug Development and Research Laboratories, Department of Pharmaceutical Sciences, Kitasato University
  • Makino Kazuishi
    Laboratory of Organic Chemistry for Drug Development and Research Laboratories, Department of Pharmaceutical Sciences, Kitasato University
  • Shimada Naoyuki
    Laboratory of Organic Chemistry for Drug Development and Research Laboratories, Department of Pharmaceutical Sciences, Kitasato University

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  • Boronic Acid-Catalyzed Final-Stage Site-Selective Acylation for the Total Syntheses of <i>O</i>-3′-Acyl Bisabolol β-D-Fucopyranoside Natural Products and Their Analogues

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<p>The first concise total syntheses of O-3′-senecioyl α-bisabolol β-D-fucopyranoside (4a) and O-3′-isovaleroyl α-bisabolol β-D-fucopyranoside (4b) were achieved through final-stage site-selective acylation via the activation of cis-vicinal diols by imidazole-containing boronic acid catalysts as a key step. This synthetic method was also effective for the syntheses of unnatural analogues with modified acyl side chains or carbohydrate moiety.</p>

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