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

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• 作者：Naoto Kinashi^a ; Kazuhiko Sakaguchi^a ; ; Shigeo Katsumura^a ; ^b ; ; Tetsuro Shinada^a
• 关键词：Ylidenebutenolide ; Eneyne ester ; Peridinin ; Ethynylstannylation ; Building block ; Ethynylacrylate
• 刊名：Tetrahedron Letters
• 出版年：2016
• 出版时间：6 January 2016
• 年：2016
• 卷：57
• 期：1
• 页码：129-132
• 全文大小：662 K

文摘

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.