Synthesis of the EF-ring of ciguatoxin 3C based on the [2,3]-Wittig rearrangement and ring-closing olefin metathesis.

Abstract

The EF-ring segment of ciguatoxin 3C, a causative toxin of ciguatera fish poisoning, was synthesized in three major steps: 1,4-addition for the C20O-C27 bond connection, chirality transferring anti selective [2,3]-Wittig rearrangement for the construction of the anti-2-hydroxyalkyl ether part, and ring-closing olefin metathesis for the F-ring formation.

• Authors: Akiyoshi Goto, Kenshu Fujiwara, Ayako Kawai, Hidetoshi Kawai, Takanori Suzuki
• Journal: Organic letters (Org Lett) Vol. 9 Issue 26 Pg. 5373-6 (Dec 20 2007) ISSN: 1523-7060 [Print] United States
• PMID: 18052179 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Alkenes
• ciguatoxin 3C
• Ciguatoxins

Topics

• Alkenes (chemistry)
• Ciguatoxins (chemical synthesis, chemistry)
• Cyclization