Chemical Research in Chinese Universities ›› 2013, Vol. 29 ›› Issue (6): 1119-1124.doi: 10.1007/s40242-013-3131-6

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Synthesis of Dihydrobenzofuran Neoligans Licarin A and Dihydrocarinatin as Well as Related Triazolylglycosides

LIU Shuang-yan, WANG Gang-qiang, LIANG Zhi-ying, WANG Qiu-an   

  1. State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China
  • Received:2013-03-20 Revised:2013-05-28 Online:2013-12-01 Published:2013-06-03
  • Contact: WANG Qiu-an E-mail:WangQA@hnu.edu.cn
  • Supported by:

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

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(36) 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.

Key words: Dihydrobenzofuran, Licarin A, Dihydrocarinatin, Triazolylglycoside