Synthesis of the Functionalized Cyclohexanecarbaldehyde Derivative. A Potential Key Compound for Total Synthesis of Optically Active Tetrodotoxin

Abstract

Abstract Oxidation of 1L-(1,2,3′,4,5/3,6)-3-hydroxymethyl-2,4,5-tri-O-methoxymethyl-3,3′-O-methylene-6-nitro-2,3,4,5-tetrahydroxycyclohexanecarbaldehyde dimethyl acetal with potassium t-butoxide and m-chloroperbenzoic acid has given corresponding carbonyl derivative in 65% yield. The carbonyl compound has been successfully converted into the desired key compound for tetrodotoxin synthesis in excellent yield via the spiro α-chloro-epoxide derivative.