Stereoselective total syntheses of (±)-arthrinone and related natural compounds

The first total syntheses of (±)-arthrinone, (±)-1-dehydroxyarthrinone, and (±)-3a,9a-deoxy-3a-hydroxy-1-dehydroxyarthrinone, antifungal metabolites from the coprophilous fungus Cercophora sordarioides, were accomplished in a stereoselective manner. The ring systems of these metabolites, which were rare among natural products, were efficiently and diastereoselectively assembled using the [2,3]Wittig rearrangement and Diels–Alder reaction as the key steps.