ChemInform Abstract: Synthesis of Siloxy‐α‐Lapachone Derivatives by Chemo‐ and Regioselective Diels—Alder Reactions of 3‐Methylene‐1,2,4‐naphthotriones with Silyl Enol Ethers.

Abstract

o-Quinone methides, generated in situ from Knoevenagel condensation of 2-hydroxy-1,4-naphthoquinone with aldehydes, readily undergo [4 + 2] cycloaddition reactions with silyl enol ethers selectively at one of the 1-oxadiene units to furnish siloxy-containing α-lapachone derivatives.