摘要/Abstract

毛蕊花苷（Acteoside）是苯丙素苷类天然产物中的代表性分子，具有广泛的生物活性.报道了一条新的合成毛蕊花苷的路线.在合成中，利用鼠李糖基邻炔基苯甲酸酯给体和2，3，4-三羟基葡萄糖硫苷在金（I）催化下的区域选择性糖苷化，得到关键的α-（1→3）连接二糖硫苷7-1，通过二糖的邻炔基苯甲酸酯给体合成苯丙素苷，进而完成了毛蕊花苷的合成.区域选择性的糖苷化减少了保护基操作步骤，缩短了合成路线.
关键词: 毛蕊花苷, 苯丙素苷, 糖苷化, 金(I)催化
A new approach to the synthesis of acteoside, a prototypical phenylpropanoid glycoside with a variety of biological activities, has been developed. The synthesis employed a regioselective glycosylation as a key step, in which a gold(I)-catalyzed glycosylation of p-tolyl 6-O-acetyl-1-thio-β-D-glucopyranoside with peracetyl L-rhamnopyranosyl ortho-alkynylbenzoate led to the desired α-(1→3) linked disaccharide 7-1 in a satisfactory yield. The resultant disaccharide was converted into the corresponding ortho-alkynylbenzoate donor and subjected to glycosylation with aglycone, subsequent deprotection of the protecting groups furnished acteoside.
Key words: acteoside, phenylpropanoid glycoside, glycosylation, Au(I) catalysis


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