Preparation of E-α-stannyl-β-trimethylsilylethynylacrylate, building block for polyconjugated ylidenebutenolide and its derivatives, by novel E-selective ethynylstannylation of propiolate

Abstract E -α-Stannyl-β-trimethylsilylethynylacrylates, which are effective building blocks for the polyconjugated ylidenebutenolides and its modified derivatives, were directly synthesized via novel E -selective ethynylstannylation of propiolic acid esters. These building blocks were applied to the syntheses of the ylidenebutenolide segment in the previous peridinin synthesis and a short chain Z -eneyne ester derivative, by the sequential Stille and Sonogashira couplings with the corresponding epoxide and vinyl iodide segments.