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

  • M. A. Gromova
  • Yu. V. Kharitonov
  • T. V. Rybalova
  • E. E. Shul’tsEmail author
Article
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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.

Keywords

diterpenoids isopimaric acid β-carbolines heterocyclic compounds Pictet–Spengler reaction XSA 

Notes

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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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • M. A. Gromova
    • 1
  • Yu. V. Kharitonov
    • 1
  • T. V. Rybalova
    • 1
    • 2
  • E. E. Shul’ts
    • 1
    • 2
    Email author
  1. 1.N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian BranchRussian Academy of SciencesNovosibirskRussia
  2. 2.Novosibirsk State UniversityNovosibirskRussia

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