本論文敘述天然物valerenic acid之形式合成。我們以烯酮74為起始物，經過1,4-加成反應與碘化反應後，得到α-碘基環酮73，以自由基環化反應為關鍵步驟建立六,五-駢環的骨架部分。再以消去反應得到化合物71，先將化合物71還原成醇後做上TBS的保護得到化合物86。將化合物86進行氫化反應隨後去除TBS的保護得到醇85。最後利用官能基轉換得到已知的中間體43，完成了天然物valerenic acid的形式合成。

A formal synthesis of valerenic acid is described. The systhesis began with 1,4-addition of enone 74 followed by iodination to provide α-iodo ketone 73. The key step involved a radical cyclization of α-iodo ketone 73 to construct the [6,5]-bicyclic skeleton. Treatment of 82 with NaI and DBU resulted in elimination of tosylate followed by reduction of enone 71 and subsequent silyl protection of alcohol 84 gave 86. Hydrogenation of 86 followed by desilylation afforded alcohol 85. Conversion of 85 into the known intermedium ketone 43 completed the formal synthesis.

目錄…………………………………………………………… i
縮寫對照表……………………………………………… ii
天然物Valerenic acid之形式全合成研究……………………………1
第一章 : 緒論
§ 1-1 Valerenic Acid 的單離、藥性及結構………………2
§ 1-2 Valerenic Acid及其衍生物的合成文獻回顧…………5
§ 1-3 Valerenic Acid之逆合成分析…………………………12
第二章 : 結果與討論
§ 2-1 六,五-駢環骨架之合成研究……………………………15
§ 2-2 Valerenic Acid之形式全合成研究……………………21
第三章 :結論..............................................32

第四章 : 實驗部分
§ 4-1 一般實驗敘述……………………………………………33
§ 4-2 實驗步驟與光譜資料……………………………………36
參考文獻……………………………………………………………..…55
附錄……………………………………………………………………58

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