First Total Synthesis of the Pavine Alkaloid (±)-Neocaryachine and Its Optical Resolution

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  • Miura Yuta
    School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University
  • Saito Yohei
    School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University
  • Goto Masuo
    Division of Chemical Biology and Medicinal Chemistry, UNC Eshelman School of Pharmacy, University of North Carolina
  • Nakagawa-Goto Kyoko
    School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University Division of Chemical Biology and Medicinal Chemistry, UNC Eshelman School of Pharmacy, University of North Carolina

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<p>The first total synthesis of (±)-neocaryachine (1) was achieved using a radical cyclization to produce the dibenzo-9-azabicyclo[3.3.1]nonane pavine skeleton, following a Bischler–Napieralski reaction to construct an intermediate benzylisoquinoline. The resulting racemic mixture was separated by chiral column chromatography to provide pure (+)- and (−)-1.</p>

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