Syntheses of stereodefined β-alkylidene-γ-lactones and substituted β, γ-unsaturated δ-lactones

1-Trimethylsilyl-1,3-diyne derived trans-bis(trimethylstannyl) enynes undergo stepwise transmetallation with methyllithium to furnish the corresponding enynyllithium reagents. The application, in various orders, of a sequence of transmetallation-protonation-alkylation-hydroxyalkylation-hydroboration-oxidation reactions provides a novel approach to stereo-defined β-alkylidene γ-lactones and β, γ-unsaturated δ-lactones.