Chemical Emulation of the Biosynthesis of (±)-Arnebidin

Abstract

We report a 13-step biomimetic total synthesis of (±)-arnebidin from 1,5-dihydroxynaphthalene. An intermolecular Diels-Alder homodimerization triggers spontaneous dehydrogenation and an intramolecular cycloaddition, delivering a single diastereomer under ambient conditions. This Diels-Alder cascade supports the proposed biosynthetic pathway and enables access to cyclopropane quinone dimers.