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Synthesis of dihydrobenzofuran neoligans licarin a and dihydrocarinatin as well as related triazolylglycosides

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Abstract

Two natural dihydrobenzofuran neolignans licarin A(1) and dihydrocarinatin(2) were systhesized from isoeugenol with Ag2O-catalyzed biomimetic oxidative coupling as the key step. Four novel dihydrobenzofuran triazolylglycoside(3–6) were achieved in good yields via Cu(I)-catalyzed azide-alkyne cycloadditions of licarin A terminal alkynes with different azide acetylated sugar and deacetylation with sodium methoxide in anhydrous methanol. The structures of all the compounds synthesized were determined by elemental analysis, MS, 1H NMR and 13C NMR. And the inhibition activity of synthesized compounds on α-glucosidase was determined by in vitro experiments. The results show that triazolyglycosides 3, 4, 5 and 6 show moderate inhibitory activity on α-glucosidase.

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Authors and Affiliations

  1. State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, P. R. China

    Shuang-yan Liu, Gang-qiang Wang, Zhi-ying Liang & Qiu-an Wang

Authors
  1. Shuang-yan Liu
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  2. Gang-qiang Wang
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  3. Zhi-ying Liang
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  4. Qiu-an Wang
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Corresponding author

Correspondence to Qiu-an Wang.

Additional information

Support by the Hunan Provincial Innovation Foundation for Postgraduate, China(No.CX2012B160) and the Personal Training Funds in National Basic Science of China(No. J1210040/J0104).

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Liu, Sy., Wang, Gq., Liang, Zy. et al. Synthesis of dihydrobenzofuran neoligans licarin a and dihydrocarinatin as well as related triazolylglycosides. Chem. Res. Chin. Univ. 29, 1119–1124 (2013). https://doi.org/10.1007/s40242-013-3131-6

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  • DOI: https://doi.org/10.1007/s40242-013-3131-6

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