Synthetic Transformations of Higher Terpenoids. 38.* Synthesis of Conjugates Containing β-Carboline and Tricyclic Diterpenoids
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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.
Keywordsditerpenoids isopimaric acid β-carbolines heterocyclic compounds Pictet–Spengler reaction XSA
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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