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Total Synthesis of Echinoside A, a Representative Triterpene Glycoside of Sea Cucumbers
Author(s) -
Chen Xiaoping,
Shao Xiaofei,
Li Wei,
Zhang Xiaheng,
Yu Biao
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201703610
Subject(s) - triterpene , glycoside , tetrasaccharide , sea cucumber , antifungal , stereochemistry , total synthesis , chemistry , yield (engineering) , biology , biochemistry , ecology , microbiology and biotechnology , polysaccharide , medicine , materials science , alternative medicine , pathology , metallurgy
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.