Practical Route to the Left Wing of CTX1B and Total Syntheses of CTX1B and 54‐deoxyCTX1B |
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| Authors: | Dr Shuji Yamashita Dr Katsutoshi Takeuchi Takuya Koyama Prof?Dr Masayuki Inoue Prof?Dr Yujiro Hayashi Prof?Dr Masahiro Hirama |
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| Affiliation: | 1. Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980‐8578 (Japan);2. Current Address: Graduate School of Pharmaceutical Sciences, University of Tokyo, Tokyo 113‐0033 (Japan);3. Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai 980‐8578 (Japan) |
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| Abstract: | Ciguatoxins, the principal causative agents of ciguatera seafood poisoning, are extremely large polycyclic ethers. We report herein a reliable route for constructing the left wing of CTX1B, which possesses the acid/base/oxidant‐sensitive bisallylic ether moiety, by a 6‐exo radical cyclization/ring‐closing metathesis strategy. This new route enabled us to achieve the second‐generation total synthesis of CTX1B and the first synthesis of 54‐deoxyCTX1B. |
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| Keywords: | ciguatoxin polycyclic ether radical reaction ring‐closing metathesis total synthesis |
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