本論文主要探討碘化鋅誘導之omega-矽炔-alpha-氰基環酮分子內環化反應。我們使用一系列的alpha-氰基環烯酮進行1,4-加成反應引入具有三甲基矽丁炔的側鍵，再將此一系列的omega-矽炔-alpha-氰酮化合物 2 經碘化鋅作用下，可進行分子內環化反應，得到建構出烯環戊烷產物3。除此之外，只要使用多延伸一個碳的Grignard試劑，即可得到化合物4，再經由相同的反應條件可獲得建構出烯環己烷產物5。此反應有著高產率、高立體及幾何選擇性之優點。這個新發展的合成方法預期可有效地應用於複雜有機化合物的合成。

Construction of a methylenecyclopentane ring is an important issue in synthesis of natural products. This thesis delineated a newly developed process toward highly functionalized methylenecyclopentanes. Recently, we developed an efficient methylenecyclopentane annulation process to construct the functionalized methylenecyclopentanes. The efficient methylenecyclopentane annulation involves a convenient 1,4-addition of (4-buty-1-nyl)trimethylsilane magnesium chloride to 2-cyano-2-cycloalkenone 1 and following a zinc iodide promoted annulation of the resulting bicyclic product 3. We also developed the process toward methylenecyclohexane annulation via compound 4 under the same condition. This annulation process can be accomplished in mild condition and the yield is high. The utility of the functionalized methylenecyclopentane annulation was also be studied.

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