Two convergent routes to the left-wing fragment of ciguatoxin CTX3C using O,S-acetals as key intermediates.
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]
Inoue
Masayuki
M
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan. inoue@ykbsc.chem.tohoku.ac.jp
Yamashita
Shuji
S
Ishihara
Yuuki
Y
Hirama
Masahiro
M
D000080:Acetals / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry; D000478:Alkylation; D002922:Ciguatoxins / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007202:Indicators and Reagents
D000080:Acetals; D000475:Alkenes; D007202:Indicators and Reagents; C466858:ciguatoxin 3C; D002922:Ciguatoxins