Practical Route to the Left Wing of CTX1B and Total Syntheses of CTX1B and 54‐deoxyCTX1B

作者: Shuji Yamashita , Katsutoshi Takeuchi , Takuya Koyama , Masayuki Inoue , Yujiro Hayashi

DOI: 10.1002/CHEM.201405629

关键词: CiguatoxinChemistrySeafood poisoningRing-closing metathesisRadical cyclizationStereochemistryMoietyTotal synthesisMetathesisEther

摘要: Ciguatoxins, the principal causative agents of ciguatera seafood poisoning, are extremely large polycyclic ethers. We report herein a reliable route for constructing left wing CTX1B, which possesses acid/base/oxidant-sensitive bisallylic ether moiety, by 6-exo radical cyclization/ring-closing metathesis strategy. This new enabled us to achieve second-generation total synthesis CTX1B and first 54-deoxyCTX1B.

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