Concise total syntheses of callistrilones A-E have been achieved from 7 and commercially available α-phellandrene (8). The synthetic strategy, which was primarily inspired by the biogenetic hypothesis, was enabled by an oxidative [3 + 2] cycloaddition followed by a Michael addition and an intramolecular nucleophilic addition to construct the target molecules. Moreover, viminalin I was also synthesized, and its absolute configuration was unambiguously confirmed.