Synthesis of the LMN-ring fragment of the Caribbean ciguatoxin C-CTX-1 |
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| Authors: | Keita Yoshikawa Masahiro Hirama |
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| Institution: | a Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan
b Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan |
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| Abstract: | Ciguatoxin C-CTX-1 was isolated as a principal causative toxin of ciguatera seafood poisoning in the Caribbean Sea, and is structurally classified as a ladder-shaped polycyclic ether. In this Letter, we report the synthesis of the tricyclic LMN-ring system of C-CTX-1. SmI2-mediated reductive cyclization efficiently constructed the seven-membered M-ring with the axially oriented 1,3-dimethyl structure. |
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| Keywords: | Ciguatoxins Polyethers Cyclizations Enol ethers Samarium iodide |
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