Total Synthesis of (−)-Tetrodotoxin from <scp>d</scp>-Glucose: A New Route to Multi-Functionalized Cyclitol Employing the Ferrier(II) Reaction toward (−)-Tetrodotoxin

Abstract

Abstract Total synthesis of (−)-tetrodotoxin (TTX) from d-glucose is described. As a critical transformation step for synthesizing TTX, a key multi-functionalized cyclitol was prepared from d-glucose employing the Ferrier(II) reaction. Stereospecific introduction of three functionalized branched chains were achieved via Peterson olefination and spiro α-chloroepoxidation of the corresponding carbonyl derivatives.