期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 61, 期 24, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202203239
关键词
De Novo Synthesis; Glycosylation; Macrocyclic Carbohydrates; Starfish Saponins; Total Synthesis
资金
- National Key Research AMP
- Development Program of China [2018YFC0310900]
- National Natural Science Foundation of China [21901251, 22031011, 21621002]
- Key Research Program of Frontier Sciences of the Chinese Academy of Sciences [ZDBS-LY-SLH030]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20020000]
- Shanghai Municipal Science and Technology Major Project, Shanghai Sailing Program [19YF1458400]
- Laboratory for Marine Drugs and Bioproducts of Qingdao National Laboratory for Marine Science and Technology [LMDBKF201803]
Starfish have developed a special type of secondary metabolite called starfish saponins to defend against predators and parasites. Among them, starfish cyclic steroid glycosides are structurally unique and pose a significant synthetic challenge.
Starfishes have evolved with a special type of secondary metabolites, namely starfish saponins, to ward off various predators and parasites; among them, the starfish cyclic steroid glycosides stand out structurally, featuring a unique 16-membered ring formed by bridging the steroidal C3 and C6 with a trisaccharide. The rigid cyclic scaffold and the congested and vulnerable steroid-sugar etherate linkage present an unprecedented synthetic challenge. Here we report a collective total synthesis of the major starfish cyclic steroid glycosides, namely luzonicosides A (1) and D (2) and sepositoside A (3), with an innovative approach, which entails a de novo construction of the ether-linked hexopyranosyl units, use of olefinic pyranoses as sugar precursors, and a decisive ring-closing glycosylation under the mild gold(I)-catalyzed conditions.
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