Phlomisoic acid reacted with methyl-1-deoxy-2,3,4-tri-O-acetyl-1-bromo-α-D-glucopyranuronate to form the 18-O-β-D-(glucuronopyranoside)-6′-O-methyl ester of 15,16-epoxylabda-8(9),13,14-triene. Reductive amination of methyl 16-formyl-15,16-epoxylabda-8(9),13,14-trienoate or this β-D-glucuronopyranoside of 16-formyl-15,16-epoxylabda-8(9),13,14-triene by propargylamine in the presence of NaBH4 gave the corresponding 16-propargylaminomethyl-15,16-epoxylabda-8(9),13,14-trienes. Copper-catalyzed azide-alkyne cycloaddition of the new terpenoid alkynes and the propargylamide of phlomisoic acid with methyl 1-deoxy-2,3,4-tri-O-acetyl-1-azido-α-D-glucopyranuronate synthesized the corresponding labdanoid glucuronides and diglucuronide. Selective screening of the labdanoid triazolylglucuronides identified compounds with analgesic activity in chemical and thermal irritation tests.
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Acknowledgment
The work was financially supported by a grant of the Russian Foundation for Basic Research (Project No. 18-03-01012). We thank the Khimiya Common Use Center, SB, RAS, for spectral and analytical studies.
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Translated from Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2020, pp. 586–594.
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Brusentseva, O.I., Kharitonov, Y.V., Dolgikh, M.P. et al. Synthesis and Analgesic Activity Assessment of Furanolabdanoid Conjugates with Glucuronic Acid. Chem Nat Compd 56, 678–687 (2020). https://doi.org/10.1007/s10600-020-03119-7
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DOI: https://doi.org/10.1007/s10600-020-03119-7