Concise synthesis of (±)-gomadalactone A

We report the synthesis of (±)-gomadalactone A, a contact sex pheromone of the white-spotted longicorn beetle ( Anoplophora malasiaca ). The synthesis employs Vassilikogiannakis' one-pot, photo-driven cyclopentenone synthesis from a furan derivative, followed by lactonization, to efficiently construct a distinctive 3-oxabicyclo[3.3.0]octane framework. This eleven-step process starts from methyl 2-furylacetate, produced (±)-gomadalactone A in an overall yield of 1 %. • Synthesis of (±)-gomadalactone A. • Employs Vassilikogiannakis' one-pot, photo-driven cyclopentenone synthesis. • Efficient construction of unique 3-oxabicyclo[3.3.0]octane structure achieved. • Required synthetic steps were significantly reduced. • Diastereomeric bicyclic lactone with potential for synthesis of gomadalactone B.