Facile Synthesis of Saikosaponins

Molecules

Ziqiang Wang¹  Tong Mu²  Biao Yu²  Peng Xu²  Bingcheng Wei² 

[1] 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;

关键词: saikosaponin;    triterpene;    glycoside;    glycosylation;    gold(I);   

DOI  :  10.3390/molecules26071941

来源: DOAJ

【 摘 要 】

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 (1–2) and their natural congeners, including prosaikosaponin F (3), G (4), saikosaponin Y (5), prosaikogenin (6), and clinoposaponin I (7). 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.

【 授权许可】

Unknown