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/oxidantsensitive 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.
| Original language | English |
|---|---|
| Pages (from-to) | 2621-2628 |
| Number of pages | 8 |
| Journal | Chemistry - A European Journal |
| Volume | 21 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - 2015 Feb 2 |
Keywords
- Ciguatoxin
- Polycyclic ether
- Radical reaction
- Ring-closing metathesis
- Total synthesis
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
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Cite this
Yamashita, S., Takeuchi, K., Koyama, T., Inoue, M., Hayashi, Y., & Hirama, M. (2015). Practical route to the left wing of CTX1B and total syntheses of CTX1B and 54-deoxyCTX1B. Chemistry - A European Journal, 21(6), 2621-2628. https://doi.org/10.1002/chem.201405629