A short (5 steps) and highly efficient (25\% overall yield) synthesis of paracaseolide A is described. Crucial steps are an alpha-iodination of a butenolide, a Suzuki coupling and a thermal Diels-Alder reaction. In attempts at Lewis acid catalyzed {[}4 + 2]-cycloadditions a set of novel dimerization products of the proposed biosynthetic paracaseolide A precursor were produced.