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Total synthesis of hamacanthin B class marine bisindole alkaloids

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Chemistry of Heterocyclic Compounds Aims and scope

A method for the synthesis of 1-(1H-indol-3-yl)ethane-1,2-diamines, key synthetic precursors of a number of marine alkaloids, has been developed based on the reduction of adducts of O-benzylhydroxylamine and N-protected 3-(2-nitrovinyl)indoles. For the first time, the total synthesis of 6’,6”-didebromohamacanthin B, 6’-debromohamacanthin B, and 6”-debromohamacanthin B, the secondary metabolites of the sponges Spongosorites and Discodermia calyx, was carried out.

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The study was carried out with the financial support of the Russian Foundation for Basic Research within the framework of scientific projects No. 17-53-10012 KO_a and No. 19-33-50009 мол_нр.

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Authors and Affiliations

  1. RUDN University, 6 Miklukho-Maklaya St, Moscow, 117198, Russia

    Nikita E. Golantsov, Alexey А. Festa, Alexandra S. Golubenkova, Khung M. Nguyen, Alexey V. Varlamov & Leonid G. Voskressensky

  2. Ufa State Petroleum Technological University, 1 Kosmonavtov St, Ufa, 450062, Russia

    Evgeniya A. Yakovenko

Authors
  1. Nikita E. Golantsov
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  2. Alexey А. Festa
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  3. Alexandra S. Golubenkova
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  4. Khung M. Nguyen
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  5. Evgeniya A. Yakovenko
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  6. Alexey V. Varlamov
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  7. Leonid G. Voskressensky
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Corresponding author

Correspondence to Nikita E. Golantsov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(3), 331–338

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Golantsov, N.E., Festa, A.А., Golubenkova, A.S. et al. Total synthesis of hamacanthin B class marine bisindole alkaloids. Chem Heterocycl Comp 56, 331–338 (2020). https://doi.org/10.1007/s10593-020-02664-x

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  • DOI: https://doi.org/10.1007/s10593-020-02664-x

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