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Facile synthesis of the azocino[4,3-b]indole framework of strychnopivotine and other Strychnos alkaloids

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Chemistry of Heterocyclic Compounds Aims and scope

A new synthetic route to the 1,5-methanoazocino[4,3-b]indole is described. The aim of the present study is to provide a tetracyclic skeleton for the synthesis of pentacyclic Strychnos alkaloids (tubifolidine and strychnopivotine). Starting from a carbazole derivative, the ring closure was achieved by an intramolecular aldol reaction. The final product was obtained in 45% in the overall yield over 7 steps.

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Financial support provided by The Scientific and Technical Research Council of Turkey (TUBİTAK) through project 112T503 is gratefully acknowledged. This research is part of Recep Yılmaz's MSc thesis.

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Authors and Affiliations

  1. Department of Chemistry, Namık Kemal University, 59030, Tekirdag, Turkey

    Nesimi Uludag & Recep Yılmaz

  2. Department of Chemical Technology, Namık Kemal University, 59700, Muratlı, Tekirdag, Turkey

    Oktay Asutay

  3. Department of Chemistry, Hitit University, 19030, Corum, Turkey

    Naki Colak

Authors
  1. Nesimi Uludag
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  2. Recep Yılmaz
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  3. Oktay Asutay
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  4. Naki Colak
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Correspondence to Nesimi Uludag.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(3), 196–199

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Uludag, N., Yılmaz, R., Asutay, O. et al. Facile synthesis of the azocino[4,3-b]indole framework of strychnopivotine and other Strychnos alkaloids. Chem Heterocycl Comp 52, 196–199 (2016). https://doi.org/10.1007/s10593-016-1860-4

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  • DOI: https://doi.org/10.1007/s10593-016-1860-4

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