於本篇論文中，本人發展新型苯炔引發反應方法以製備一系列烯類及烯醇式醋酸酯並完成數個1-去氧酮醣之全合成研究。除此之外，本人提出一個新的概念將光引導去氧核醣核酸切割試劑與分子信號燈相結合，形成一新型具有切割去氧核醣核酸能力之新型生物分子。
在本論文第一部分A章節中，本人報導具立體專一性之新型苯炔引發烯化反應。使用□-胺基醇作為起始物與二硫化碳反應之後，再與苯炔進行反應可以成功形成烯類化合物。此一新方法之反應機構為[2 + 3]環化反應與反向之[2 + 3]環化反應。
在第一部分B章節中，利用新發展之合成策略本人成功合成出九個新型之烯醇式醋酸酯。本人亦報導使用這些烯醇式醋酸酯作為關鍵中間物以完成數個1-去氧酮醣之全合成研究。
在第二部分，光引導去氧核醣核酸切割試劑藉由醯胺鍵的生成及硫醇和馬林亞醯胺所產生之Micheal加成反應與分子信號燈相結合，形成一新型具有切割去氧核醣核酸能力之生物分子。

English Abstract……………………i
Chinese Abstract………………ii
Acknowledgement……………………iii
Contents……………………………iv
Part I: (A) Stereospecific Benzyne-Induced Olefination from □-Amino Alcohols……………………1
Abstract…………………………2
Introduction………………………………3
Results……………………………… 4
Discussion……………………………9
Conclusion……………………………………11
Experimental Section…………………………12
References………………………26
Part I: (B) Syntheses of Enol Acetates through Benzyne-Induced Addition–Elimination and their Synthetic Applications……………………28
Abstract……………………………29
Introduction……………………………30
Results ……………………………………32
Discussion……………………………38
Conclusion………………………………………42
Experimental Section…………………………………43
References………………………………………………63
Part II: Syntheses of Molecular Beacon-type DNA-Cleaving Agent ………………………………………66
Abstract………………………………………………67
Introduction………………………………68
Results……………………………70
Discussion……………………………………………77
Conclusion ………………………………84
Experimental Section…………………………85
References…………………………………………………96
Spectra………………………………98

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