Practical route to the left wing of CTX1B and total syntheses of CTX1B and 54-deoxyCTX1B
Shuji Yamashita1, Katsutoshi Takeuchi, Takuya Koyama
1Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578 (Japan). syamashita@fas.harvard.edu.
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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