title: Practical route to the left wing of CTX1B and total syntheses of CTX1B and 54-deoxyCTX1B.
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.
authors.affiliation: Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578 (Japan). syamashita@fas.harvard.edu.
authors.forename: Shuji
authors.initials: S
authors.lastname: Yamashita
authors.forename: Katsutoshi
authors.initials: K
authors.lastname: Takeuchi
authors.forename: Takuya
authors.initials: T
authors.lastname: Koyama
authors.forename: Masayuki
authors.initials: M
authors.lastname: Inoue
authors.forename: Yujiro
authors.initials: Y
authors.lastname: Hayashi
authors.forename: Masahiro
authors.initials: M
authors.lastname: Hirama
mesh_terms: D002922:Ciguatoxins / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004987:Ethers / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D011789:Quantum Theory; D012451:Safrole / Q000031:analogs & derivatives / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004987:Ethers; D005609:Free Radicals; C454647:ciguatoxin 1B (CTX 1B); D002922:Ciguatoxins; D012451:Safrole; C005746:sulfoxide
keywords: ciguatoxin; polycyclic ether; radical reaction; ring-closing metathesis; total synthesis