Convergent Total Synthesis of Caribbean Ciguatoxin C‑CTX1 and Its C3-Epimer

Makoto Sasaki, Atsushi Umehara, Kohtaro Sugahara, Masayuki Satake, Takeshi Tsumuraya · Journal of the American Chemical Society · 2026

Explore this paper's citation graph

Summary

This is the first total synthesis of C-CTX1 and its naturally occurring C3-epimer through a convergent fragment-coupling strategy joining the ABCDE- and HIJKLMN-ring units, featuring late-stage radical cyclization and ring-closing metathesis to construct the central FG-rings.

Type: article
Published: 2026-03-09
Cited by: 3
References: 41
Access: Open access
DOI: https://doi.org/10.1021/jacs.6c01247
PubMed: https://pubmed.ncbi.nlm.nih.gov/41802301/
PMC: https://www.ncbi.nlm.nih.gov/pmc/articles/13022860/
OpenAlex: https://openalex.org/W7134813809
Semantic Scholar: https://api.semanticscholar.org/CorpusID:286426443

Keywords

Total synthesis, Ciguatoxin, Ciguatera, Marine toxin, Convergent synthesis

References

Practical route to the left wing of CTX1B and total syntheses of CTX1B and 54-deoxyCTX1B.Antonio Henríquez Jiménez — 2015
Total Synthesis of Ciguatoxin CTX3CMasahiro Hirama, Tohru Oishi, Hisatoshi Uehara — 2001
Ciguatoxin: Isolation and Chemical NaturePaul J. Scheuer, Wataru Takahashi, Junzo Tsutsumi — 1967
Convergent strategies for syntheses of trans-fused polycyclic ethers.Masayuki Inoue — 2005
Structures of ciguatoxin and its congenerMichio Murata, Anne Legrand, Yoshihiko Ishibashi — 1989
Organoaluminum-promoted Beckmann rearrangement of oxime sulfonatesKeiji Maruoka, T. Miyazaki, Mamoru Ando — 1983
Intramolecular radical cyclization-ring-closing metathesis approach to fused polycyclic ethers. Convergent synthesis and conformational analysis of the (E)FGH ring system of ciguatoxin.Makoto Sasaki, Tetsuji Noguchi, Kazuo Tachibana — 2002
Total synthesis of marine polycyclic ethers.Tadashi Nakata — 2005
Total synthesis of ciguatoxin and 51-hydroxyCTX3C.Masayuki Inoue, Keisuke Miyazaki, Yuuki Ishihara — 2006
Ciguatera: Australian perspectives on a global problem.Richard J. Lewis — 2006
Structures and Configurations of Ciguatoxin from the Moray Eel Gymnothorax javanicus and Its Likely Precursor from the Dinoflagellate Gambierdiscus toxicusMichio Murata, Anne Legrand, Yoshihiko Ishibashi — 1990
Marine neurotoxins: state of the art, bottlenecks, and perspectives for mode of action based methods of detection in seafood.Jonathan Nicolas, Peter J.M. Hendriksen, Arjen Gerssen — 2014
Structure of Caribbean Ciguatoxin Isolated from Caranx latusRichard J. Lewis, Jean‐Paul Vernoux, Ian M. Brereton — 1998
Convergent total syntheses of gambierol and 16-epi-gambierol and their biological activities.Isao Kadota, Hiroyoshi Takamura, Kumi Sato — 2003
The structure of CTX3C, a ciguatoxin congener isolated from cultured Gambierdiscus toxicusMasayuki Satake, Michio Murata, Takeshi Yasumoto — 1993
Total synthesis of ciguatoxin.Akinari Hamajima, Minoru Isobe — 2009
Facile Preparation of Nucleoside-5'-carboxylic Acids.Jeffrey B. Epp, Theodore S. Widlanski — 1999
Evolution of a practical total synthesis of ciguatoxin CTX3C.Masayuki Inoue, Masahiro Hirama — 2004
Improved procedure for the reductive acetylation of acyclic esters and a new synthesis of ethers.David J. Kopecky, Scott D. Rychnovsky — 2000
Stereoselective 6-exo radical cyclization using cis-vinyl sulfoxide: practical total synthesis of CTX3C.Shuji Yamashita, Yuuki Ishihara, Hiroyuki Morita — 2011

Cited by

Total Synthesis of (–)-Ciguatoxin C-CTX1Erick M. Carreira, Alexander Hamminger — 2026

Related papers

No related papers recorded.