A novel synthetic approach towards the recently reported anti-tumor and anti-tuberculor natural product ottelione A from the readily available Diels-Alder adduct of cyclopentadiene and p-benzoquinone is delineated. Our short strategy, besides being enantio-, regio-and stereoselective, charts an eventful course and is inherently well-suited for adaptation towards diverse synthetic analogues of this biologically potent natural product.