Two Convergent Routes to the Left-Wing Fragment of Ciguatoxin CTX3C Using <i>O</i>,<i>S</i>-Acetals As Key Intermediates

Abstract

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]