本論文主要是針對Histrionicotoxins家族化合物所具有的spiropiperidine骨架進行合成策略的探討,我們提出不同於之前所報導的合成路徑。以環己戊酮 31為起始物經由三步化學反應後得到碘化物111，接著在路易士酸促進下進行分子內合環反應形成5,6-螺旋環化合物 113，最後以Beckmann重排反應引入氮原子，得到結構近似spiropiperidine的內醯胺中間體120，此化合物未來將可應用於Histrionicotoxins家族化合物的全合成中。
An alternative synthetic strategy of spiropiperidine skeleton of Histrionicotoxins was proposed in this thesis. Cyclopentanone 110 was transferred to iodide 111 which cyclized in an intramolecular fashion with the promotion of aluminum chloride to get the spirocompound 113. Finally, the Beckmann rearrangement reaction was used to insert the nitrogen into the molecule and the spirolactam 120 was obtained successfully which was similar to the spiropiperidine in structure. The spirolactam 120 was suggested an important and versatile intermediate toward the total synthesis of members of Histrionicotoxins.
