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The one-pot construction of runctionalized α′-methoxy-γ-pyrones is detailed. Starting from α,α′-dimethoxy-γ-pyrone, molecular diversity is attained by a regio- and stereoselective desymmetrization using allyllitnium foflowed by vinylogous aldol reaction. Mechanistic considerations including density functional theory calculations and insightful experiments have been gathered to shed light on this complex multistep process. To illustrate the versatility of this methodology, some of the molecules prepared were evaluated for their ability to inhibit NADH-oxidase and NADH-ubiquinone osridoreductase. In the process, a potent new inihibitor of NADH-oxidase activity (IC 44 nM) was identified. [ABSTRACT FROM AUTHOR]