title: Two convergent routes to the left-wing fragment of ciguatoxin CTX3C using O,S-acetals as key intermediates.
abstract: Ciguatoxins, principal causative toxins of ciguatera seafood poisoning, are large ladderlike polycyclic ethers. Here, we report two convergent routes to synthesis of the multiolefinic left half of ciguatoxins based on a newly developed acyl radical strategy. Remarkably, only 13 steps from the monocyclic E-ring were required to construct the left wing. [reaction: see text]
authors.affiliation: Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan. inoue@ykbsc.chem.tohoku.ac.jp
authors.forename: Masayuki
authors.initials: M
authors.lastname: Inoue
authors.forename: Shuji
authors.initials: S
authors.lastname: Yamashita
authors.forename: Yuuki
authors.initials: Y
authors.lastname: Ishihara
authors.forename: Masahiro
authors.initials: M
authors.lastname: Hirama
mesh_terms: D000080:Acetals / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry; D000478:Alkylation; D002922:Ciguatoxins / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007202:Indicators and Reagents
chemical_list: D000080:Acetals; D000475:Alkenes; D007202:Indicators and Reagents; C466858:ciguatoxin 3C; D002922:Ciguatoxins