柴胡皂苷的简便合成
Facile Synthesis of Saikosaponins.
作者信息
Wang Ziqiang, Wei Bingcheng, Mu Tong, Xu Peng, Yu Biao
机构信息
Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei 230026, China.
State Key Laboratory of Bio-organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
出版信息
Molecules. 2021 Mar 30;26(7):1941. doi: 10.3390/molecules26071941.
Saikosaponin A (SSa) and D (SSd) are typical oleanane-type saponins featuring a unique 13,28-epoxy-ether moiety at D ring of the aglycones, which exhibit a wide range of biological and pharmacological activities. Herein, we report the first synthesis of saikosaponin A/D (-) and their natural congeners, including prosaikosaponin F (), G (), saikosaponin Y (), prosaikogenin (), and clinoposaponin I (). The present synthesis features ready preparation of the aglycones of high oxidation state from oleanolic acid, regioselective glycosylation to construct the β-(1→3)-linked disaccharide fragment, and efficient gold(I)-catalyzed glycosylation to install the glycans on to the aglycones.
柴胡皂苷A（SSa）和D（SSd）是典型的齐墩果烷型皂苷，苷元的D环具有独特的13,28 - 环氧醚部分，表现出广泛的生物学和药理活性。在此，我们报道了柴胡皂苷A/D（-）及其天然同系物的首次合成，包括前柴胡皂苷F（）、G（）、柴胡皂苷Y（）、前柴胡皂苷元（）和棉根皂苷I（）。本合成方法的特点是从齐墩果酸容易制备高氧化态的苷元，区域选择性糖基化构建β -（1→3）连接的二糖片段，以及高效的金（I）催化糖基化将聚糖连接到苷元上。
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