Convergent Synthesis of the WXYZA′B′C′D′E′F′ Ring Segment of Maitotoxin

Abstract

Abstract Synthesis of the WXYZA′B′C′D′E′F′ ring segment of maitotoxin, a ladder-shaped polyether produced by the dinoflagellate Gambierdiscus toxicus, was achieved based on a convergent strategy via α-cyano ethers developed in our laboratory. The WXYZ ring aldehyde and the C′D′E′F′ diol were combined through the construction of the B′ ring via ring-closing metathesis and the A′ ring via O,S-acetal formation followed by radical reduction. Introduction of a terminal olefin in the side chain culminated in the convergent synthesis of the WXYZA′B′C′D′E′F′ ring segment in 16 steps.