本論文含兩部分 : 第一部份是利用樟腦醯胺為掌性輔助基進行甘胺酸酯之不對稱 1,4-加成反應生成具光學活性之焦谷胺酯，並應用在紅藻胺酸 (+)-α-Allokainic acid 1和C2-epi-紅藻胺酸 (-)-2-epi-α-Allokainic acid 2的全合成研究上;第二部分則是利用具光學活性之焦谷胺酯，來進行生物鹼 (-)-Isoretronecanol 3，(+)-Laburnine 4 和 (+)-turneforcidine 5的全合成研究。

一.紅藻胺酸1和立體異構物2的全合成:利用樟腦醯胺為掌性輔助基之亞胺6與α，β-不飽和酸酯7進行不對稱1,4-加成反應，經由後續的合成策略，共需11項步驟合成出紅藻胺酸(+)-α-Allokainic acid 1和C2-epi-紅藻胺酸(-)-2-epi-α-Allokainic acid 2，總產率分別為17.8和18% 。
二.生物鹼 (-)-Isoretronecanol 3，(+)-Laburnine 4 和 (+)-turneforcidine 5的全合成: 利用樟腦醯胺為掌性輔助基之亞胺6與α，β-不飽和酸酯8進行不對稱1,4-加成反應，並應用在生物鹼 (-)-Isoretronecanol 3，(-)-Laburnine 4 和 (+)-turneforcidine 5的全合成上。合成(-)-Isoretronecanol 3和(+)-Laburnine 4共花9個步驟，並以亞胺6作為起始物，總產率分別為17 %和17.9 %。合成(+)-turneforcidine 5共花9個步驟，總產率為13.0%。

The studies on the applications of camphor derivatives as chiral auxiliaries in the synthesis of natural products are described. This thesis consists of two parts. The first part describes an application of imine 6 derived from glycinate and ketoamide in total syntheses of (+)-α-Allokainic acid 1 and (–)-2-epi- α-Allokainic acid 2. The second part describes the asymmetric 1,4 addition of imine 6, and application on total syntheses of pyrrolizidine-type alkaloids

(1) Total syntheses of (+)-α-Allokainic acid 1 and (–)-2-epi- α-Allokainic acid 2: (+)-α-Allokainic acid 1 and (–)-2-epi- α-Allokainic acid 2 have been prepared in 11 steps from imine 6, respectively. The total yield of these two compounds are 17.8 or 18.0 %, respectivelty.

(2) Total synthesis of pyrrolizidine Alkaloids (–)-Isoretronecanol 3, (+)-Laburine 4, and (+)-Turneforcidine 5: (–)-Isoretronecanol 3 and (+)-Laburine 4 have been prepared from 6 in nine steps. Total yield of 3 and 4 are 17.0 and 17.9 %, respectivelty. (+)-Turneforcidine 5 have been prepared from 6 in nine steps. Total yield of 5 is 13.0 %.

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