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      A Fast Assembly of Pentacyclic Benz[f]indolo[2,3-a]quinolizidine Core by Tandem Intermolecular Formal Aza-[3 + 3] Cycloaddition/Pictet−Spengler Cyclization:  A Formal Synthesis of (±)-Tangutorine

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      The Journal of Organic Chemistry

      American Chemical Society (ACS)

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          Abstract

          <p class="first" id="d23157885e65">We have described a concise construction of the pentacyclic benz[f]indolo[2,3-a]quinolizidine intermediate 3 (with an overall yield of 54% for three steps), featuring a tandem intermolecular formal aza-[3 + 3] cycloaddition/Pictet-Spengler cyclization. The present work can be considered as a formal synthesis of beta-carboline alkaloid (+/-)-tangutorine. Our strategy disclosed herein constitutes a new effective general synthetic approach toward the indoloquinolizidine family of alkaloids. </p>

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          Author and article information

          Journal
          The Journal of Organic Chemistry
          J. Org. Chem.
          American Chemical Society (ACS)
          0022-3263
          1520-6904
          June 2004
          June 2004
          : 69
          : 13
          : 4548-4550
          Article
          10.1021/jo049459s
          15202919
          6a8a1acb-cebf-40b7-8f21-988c51e91a9e
          © 2004
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