本論文利用樟腦醯胺168作為掌性輔助基，與甘胺酸第三丁酯171形成之樟腦醯基亞胺135作為起始物，與α,β-不飽和酸酯149經由1,4-加成反應建構立體中心，得到非鏡像選擇性[(2S, 3S) vs (2R, 3S)]大於20 : 1之加成物159。接著利用胺轉換法將掌性輔助基水解並進行分子內合環反應，合成內醯胺(lactam)結構的焦谷胺酯 (pyroglutamate) 179，藉由羥醛反應建立出C4位置具有不對稱中心的紅藻胺酸前驅物189，作為合成紅藻胺酸(+)-α-Allokainic acid 22合成研究的重要前驅物。

This thesis describes the application of imine 135 that derived from the condensation of ketopinic amide 168, a chiral auxiliary, and tert-butyl glycinate 171 in the synthesis of pyrrolidine alkaloids. Asymmetric Michael addition of imine 135 with α,β-unsaturated ester 149 afforded adduct 159 as a diastereomeric mixture (>20 : 1). Transamination of adduct 159, followed by cyclization provided lactam 179. The construction of C4 stereogenic center was achieved by aldol reaction of Boc-protected lactam 179 with activated acetone. Further functional group transformations afforded compound 189 which is an important precursor for the synthesis of (+)-α-allokainic acid 22.

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