Enyne Coupling as the Potent Methodology for the Synthesis of Bioactive Molecules

The enyne coupling methodology for the synthesis of various sorts of substituted γ-butyrolactones from allylic alkynoates under the catalysis of PdX₂ was developed. For α,β,γ-trisubstituted γ-butyrolactones, the β,γ-relative stereochemistry can be controlled by the substituent on the triple bond of the alkynoates and a chiral center is easily introduced from the optically active allylic alcohols. For α,β-disubstituted γ-butyrolactones, the optically active products can be obtained by the resolution of the key intermediates, lactonic aldehydes, via their tartrate acetal derivatives.

palladium catalyst - enyne coupling - allylic alkynoates - lactones - stereoselective