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.