本論文內容分為兩大部分：第一部份我們參與了生物技術中心製藥流程改良，利用硒吩與琥珀氯進行Friedel-Crafts acylation反應製備1,4-雙酮基的硒吩化合物18，再與甲基羥基胺及醋酸鈉進行關環反應形成N-甲基派咯硒吩化合物20，獲得目標化合物D-501036的主要中間體結構；如此便可以五步迅速地完成D-501036的製備。
第二部分我們報導天然物10-isocyano-4-cadinene (30)、10-isothiocyanato-4-cadinene (31)、10-isothiocyanatocadin-6-ene (32)之全合成研究結果。以市售可得(-)-β-pinene (44)為起始物，合成親雙烯化合物55，再將其與異戊二烯進行Diels-Alder反應，可建立天然物所需雙環骨架；再藉雙鍵轉移及本實驗室所開發之開環步驟等的關鍵步驟，我們目前是以12步完成具光學活性的天然物α-cadinol (39)、T-cadinol (41)之全合成；距離合成天然物30、31、32尚各有一步之差。

The first part of this thesis describes the research towards an optimized synthesis process for D-501036 in support of the drug discovery efforts of the Development Center for Biotechnology. Diketone 18 was obtained via a Freidel-Crafts acylation process starting with selenophene and succinic chloride which was subsequently condensed with methylamine hydrochloride in the presence of sodium acetate to form the highly congested N-methyl pyrrolo compound 20. Pyrrole 20 was transformed to the target molecule D-501036 in 3 steps. In this way, a 5 step process towards this highly novel therapeutically valuable compound was developed.

The second part of this thesis details the investigation towards the asymmetric total synthesis of naturally occurring sesquiterpenoids of the cadinene family, namely 10-isocyano-4-cadinene (30), 10-isothiocyanato-4-cadinene (31), and 10-isothiocyanatocadin-6-ene (32). The total synthesis approach called for the generation of dienophile 55 from commercially available (-)-□-pinene (44), Diels-Alder cycloaddition of 55 with isoprene to construct the decalin core, followed by a sequence of reactions to arrive at naturally occurring trans-decalins □-cadinol (39) and T-cadinol (41), which were readily separated. With these epimeric alcohols in hand, it is believe that the final transformations (i.e. 39 □ 30, 31 and 41 □ 32) will be arrived at trivially.

中文摘要………………………………………………………………...I
英文摘要...……………………………………………………………. III
謝誌……………………………………………………………………...V
縮寫對照表…………………………………………………...………...VI
目錄………………………………………………………………..…VIII
第一章 抗癌化合物D-501036之合成研究………….………………..1
第一節 緒論…………………………………………………1
第二節 結果與討論…………………………………………6
第三節 結論………………………………………………..17
第二章 Cadinane類倍半萜天然物之合成研究…………………..19
第一節 緒論…………………...…………………………...19
1.1 天然物相關簡介……………………………….……....19
1.2 相關合成方法與逆合成分析…………………….……25
第二節 結果與討論……………………………….…….....31
第三節 結論………………………………………………..60
參考文獻………………………………………………….…...………..62
第三章：實驗部份……………………………………………...……….66
3.1 一般實驗敘述……………………………………………...………66
3.2 實驗步驟與光譜資料……………………………………...………69
附錄 光譜資料………………………………………...………….93
附錄一……………………….. ………………...………………93
附錄二 1H, 13C, DEPT 及 2D, NOE 光譜圖….…………...101

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