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’ts

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2 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)871-877
Number of pages7
JournalChemistry of Natural Compounds
Volume55
Issue number5
DOIs
Publication statusPublished - 1 Sep 2019

Keywords

  • diterpenoids
  • heterocyclic compounds
  • isopimaric acid
  • Pictet–Spengler reaction
  • XSA
  • β-carbolines
  • beta-carbolines
  • DESIGN
  • Pictet-Spengler reaction
  • DERIVATIVES
  • MOLECULES

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