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

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 cycloa...

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Bibliographic Details
Published in:Chemical research in Chinese universities 2013-12, Vol.29 (6), p.1119-1124
Main Authors: Liu, Shuang-yan, Wang, Gang-qiang, Liang, Zhi-ying, Wang, Qiu-an
Format: Article
Language:English
Subjects:
Analytical Chemistry
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Inorganic Chemistry
Organic Chemistry
Physical Chemistry
α-葡萄糖苷酶
二氢苯并呋喃
仿生催化
合成
抑制活性
新木脂素
氧化偶联
脱乙酰化
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Summary: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.
ISSN:1005-9040
2210-3171
DOI:10.1007/s40242-013-3131-6