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Synthetic Transformations of Higher Terpenoids. 38.* Synthesis of Conjugates Containing β-Carboline and Tricyclic Diterpenoids

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Chemistry of Natural Compounds Aims and scope

The synthesis and properties of tricyclic pimaranes containing a C-16 β-carboline are reported. A Pictet–Spengler reaction of methyl 15-oxo-16-formylisopimarate (prepared in situ from the 15-oxo-15,16-dihydroisopimarate) and tryptamine or tryptophan methyl ester in the presence of trifluoroacetic acid formed a mixture of terpenoid 1,2,3,4-tetrahydro-β-carbolines, 3,4-dihydro-β-carbolines, and β-carbolines. Tetrahydro- and dihydro-β-carbolines in CHCl3 were oxidized to the corresponding β-carbolines by treatment in air with basic Al2O3.

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Acknowledgment

The work was financially supported by RFBR Grants No. 17-43-543235 (p_mol_a) and No. 18-03-01012. Analytical and spectral studies were performed at the Khimiya Common Use Center at IOC, SB, RAS.

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Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, 9 Lavrent’eva Prosp, Russia

    M. A. Gromova, Yu. V. Kharitonov, T. V. Rybalova & E. E. Shul’ts

  2. Novosibirsk State University, 1 Pirogova St, Novosibirsk, 630090, Russia

    T. V. Rybalova & E. E. Shul’ts

Authors
  1. M. A. Gromova
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  2. Yu. V. Kharitonov
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  3. T. V. Rybalova
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  4. E. E. Shul’ts
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Corresponding author

Correspondence to E. E. Shul’ts.

Additional information

For No. 37, see the literature [1].

Translated from Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2019, pp. 749–755.

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Gromova, M.A., Kharitonov, Y.V., Rybalova, T.V. et al. Synthetic Transformations of Higher Terpenoids. 38.* Synthesis of Conjugates Containing β-Carboline and Tricyclic Diterpenoids. Chem Nat Compd 55, 871–877 (2019). https://doi.org/10.1007/s10600-019-02836-y

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  • DOI: https://doi.org/10.1007/s10600-019-02836-y

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