本論文研究掩飾鄰苯醌(masked o-benzoquinones)的nitroso-Diels-Alder反應並利用此方法去設計合成出多樣化的conduramine類化合物，內容分為兩部份：第一部份為掩飾鄰苯醌之不對稱nitroso-Diels-Alder反應與探討並解決亞硝基與掩飾鄰苯醌所生成的產物，其雙甲氧基無法之水解之問題；第二部份為利用第一部份所開發出之方法合成出ent-conduramine A-1 tetraacetate、(+)-conduramine A-1、(+)-conduramine E-1和(+)-ent-conduramine F-1。
在第一章中，我們利用右旋樟腦磺酸合成出右旋樟腦醯亞硝與掩飾鄰苯醌進行不對稱hetero-Diels-Alder反應，可獲得高產率的環加成產物，且非鏡像選擇性高達99%。且當掩飾鄰苯醌上的取代基位置不同，其主要產物即不同，佐以ORTEP圖譜，我們推測出比旋值與絕對組態之關連性。另一方面，懸宕已久之亞硝基與掩飾鄰苯醌反應所生成的環加成產物其雙甲氧基無法水解的問題，終於在將胺基改成疊氮基後順利解決並發現了新穎的重排反應。
第二章則是分別以右旋與左旋樟腦醯亞硝與具有MOM保護的酚衍生物II-37與進行不對稱heterto-Diels-Alder反應，歷經十步完成了ent-conduramine A-1 tetraacetate之合成，另歷經八步完成(+)-conduramine A-1之合成。另外以2-甲氧基酚II-41與右旋樟腦醯亞硝為起始物，利用於第一章發現之新穎重排反應設計合成出(+)-Conduramine E-1和(+)-ent-Conduramine F-1。

The thesis concerns with the nitroso-Diels Alder (NDA) reactions of masked o-benzoquinones (MOBs) and application of this methodology to synthesize many kinds of conduramines. The thesis contain two major aspects : the first part concerned with the asymmetric nitroso-Diels-Alder (ANDA) reactions of MOBs and solving the hydrolyzing problem of NDA adducts. The second part applies the methodologies developed in the first part to furnish the syntheses of ent-conduramine A-1 tetraacetate, (+)-conduramine A-1, (+)-conduramine E-1 and (+)-ent-conduramine F-1.
In the first chapter, we found ANDA reactions of MOBs with (+)-ketopinohydroxamic acid derived from (+)-camphorsulfonic acid
shows the high yield and disastereoselectivities, the value of diastereomeric excess is up to 99 %. Interestingly, the major product is decided by the substituent on the MOB. With the evidences of ORTEP diagrams, we got the relationship between specific rotation and absolute configuration of these compounds. Furthermore, we solve the hydrolyzing problem of NDA adducts till we change the amino group to azide group, and we got a new rearrangement product.
Utilizing the methodology of ANDA reactions of catechol has one MOM protection with (+)-ketopinohydroxamic and (-)-ketopinohydroxamic acid to furnish the syntheses of ent-conduramine A-1 tetraacetate and (+)-conduramine A-1, these are obtained from ten steps and eight steps separately. After getting the ANDA adduct from guaiacol and (+)-ketopinohydroxamic acid, we applied the methodology of new rearrangement developed in the first chapter to synthesize (+)-conduramine E-1 and (+)-ent-conduramine F-1 with ten steps and eight steps separately.

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