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

作　　者：LIU Shuang-yan WANG Gang-qiang LIANG Zhi-ying WANG Qiu-an 

机构地区：[1]State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering,Hunan University, Changsha 410082, P.R.China

出　　处：《Chemical Research in Chinese Universities》2013年第6期1119-1124,共6页高等学校化学研究（英文版）

摘　　要：Two natural dihydrobenzofuran neolignans licarin A（1） and dihydrocarinatin（2） were systhesized from isoeugenol with Ag20-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 ~3C NMR. And the inhibition activity of synthesized compounds on a-glucosidase was determined by in vitro experiments. The results show that triazolyglycosides 3, 4, 5 and 6 show moderate inhibitory activity on a-glucosidase.Two natural dihydrobenzofuran neolignans licarin A（1） and dihydrocarinatin（2） were systhesized from isoeugenol with Ag20-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 ~3C NMR. And the inhibition activity of synthesized compounds on a-glucosidase was determined by in vitro experiments. The results show that triazolyglycosides 3, 4, 5 and 6 show moderate inhibitory activity on a-glucosidase.

关 键 词：DIHYDROBENZOFURAN Licarin A Dihydrocarinatin Triazolylglycoside 

分 类 号：TQ251.1[化学工程—有机化工] TQ925.5[轻工技术与工程—发酵工程]