Total Synthesis of the Sesquiterpene (±)-Illudin C via an Intramolecular Nitrile Oxide Cycloaddition

A convergent total synthesis of illudin C is described. The tricyclic ring system of the natural product was quickly assembled from cyclopropane and cyclopentene precursors via a novel oxime dianion coupling reaction and a subsequent intramolecular nitrile oxide−olefin cycloaddition.