Total Synthesis of Echinoside A, a Representative Triterpene Glycoside of Sea Cucumbers. (31st May 2017)

• Record Type: Journal Article
• Authors: Chen, Xiaoping; Shao, Xiaofei; Li, Wei; Zhang, Xiaheng; Yu, Biao
• Is Part Of: Angewandte Chemie. Volume 129:Number 26(2017)
• Page Start: 7756
• Page End: 7760
• Publication Date: 2017-05-31
• Subjects: Glykosylierungen -- Gold -- Holostan-Glykoside -- Marine Naturstoffe -- Totalsynthesen; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201703610
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Echinoside A, a sulfonylated holostane tetrasaccharide with potent anticancer and antifungal activity, was synthesized in a longest linear sequence of 35 steps and 0.6 % overall yield. The synthetic approach is adaptable to the synthesis of congeners and analogues, as exemplified by the ready synthesis of ds‐echinoside A and echinoside B, and thus will facilitate in‐depth studies on the promising biological effects of echinoside A. Moreover, the present synthesis demonstrates the feasibility of synthetic access to the characteristic complex triterpene glycosides that occur ubiquitously in sea cucumbers.