Journal
TETRAHEDRON LETTERS
Volume 107, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2022.154102
Keywords
Cnicin; Total synthesis; Olefin metathesis; Barbier reaction
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This study examined the synthesis of cnicin using the Evans syn aldol reaction, the indium-promoted diastereoselective Barbier reaction, and ring-closing metathesis (RCM). While RCM did not afford the natural form of cnicin as the major product, the synthesis of modified cnicin was achieved.
Cnicin is a germacranolide sesquiterpene lactone with a 10-membered ring, two internal olefins, two exo olefins, and an ester side chain. The natural product is a potent inhibitor of Trypanosoma brucei, which causes human African trypanosomiasis. This study examined the synthesis of cnicin via the Evans syn aldol reaction, the indium-promoted diastereoselective Barbier reaction, and ring-closing metathesis (RCM). While RCM did not afford natural (1E)-form as the major product, the synthesis of (1Z)-deacylc-nicin was achieved.(c) 2022 Elsevier Ltd. All rights reserved.
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