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Stereoselective 6-exo radical cyclization using cis-vinyl sulfoxide: practical total synthesis of CTX3C.

Abstract
Ciguatoxins, the principal causative toxins of ciguatera seafood poisoning, are large ladder-like polycyclic ethers. We report a highly stereoselective 6-exo radical cyclization/ring-closing olefin metathesis sequence to construct the syn/trans-fused polyether system. The new method was applied to the practical synthesis of ciguatoxin CTX3C.
AuthorsShuji Yamashita, Yuuki Ishihara, Hiroyuki Morita, Junichi Uchiyama, Katsutoshi Takeuchi, Masayuki Inoue, Masahiro Hirama
JournalJournal of natural products (J Nat Prod) Vol. 74 Issue 3 Pg. 357-64 (Mar 25 2011) ISSN: 1520-6025 [Electronic] United States
PMID21250701 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Sulfoxides
  • Vinyl Compounds
  • ciguatoxin 3C
  • Ciguatoxins
Topics
  • Ciguatera Poisoning (etiology)
  • Ciguatoxins (chemical synthesis, chemistry, pharmacology)
  • Cyclization
  • Models, Molecular
  • Molecular Structure
  • Seafood (poisoning)
  • Stereoisomerism
  • Structure-Activity Relationship
  • Sulfoxides (chemistry)
  • Vinyl Compounds (chemistry)

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