有机化学 ›› 2020, Vol. 40 ›› Issue (10): 3439-3445.DOI: 10.6023/cjoc202004052 上一篇    下一篇

所属专题: 黄乃正院士七十华诞专辑

研究论文

一条合成毛蕊花苷的新路线

胡志飞a,b, 徐鹏b, 俞飚a,b   

  1. a 上海科技大学物质科学与技术学院 上海 201210;
    b 中国科学院上海有机化学研究所 生命有机化学国家重点实验室 上海 200032
  • 收稿日期:2020-04-30 修回日期:2020-05-13 发布日期:2020-05-20
  • 通讯作者: 俞飚 E-mail:byu@sioc.ac.cn
  • 基金资助:
    国家重点研发计划(No.2018YFC0310900)、国家自然科学基金(No.21621002)、中国科学院前沿科学重点研究(No.ZDBS-LY-SLH030)、中国科学院战略性先导科技专项(B类)(No.XDB20020000)和王宽诚教育基金会资助项目.

A New Approach to the Synthesis of Acteoside

Hu Zhifeia,b, Xu Pengb, Yu Biaoa,b   

  1. a School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210;
    b State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
  • Received:2020-04-30 Revised:2020-05-13 Published:2020-05-20
  • Supported by:
    Project supported by the National Key Research & Development Program of China (No. 2018YFC0310900), the National Natural Science Foundation of China (No. 21621002), the Key Research Program of Frontier Sciences of Chinese Academy of Sciences (No. ZDBS-LY-SLH030), the Strategic Priority Research Program of Chinese Academy of Sciences (No. XDB20020000), and the K. C. Wong Education Foundation.

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