Title

樟腦醯胺為掌性輔助基應用於 (+)-2-epi-α-Allokainic Acid 之不對稱合成研究

Translated Titles

Asymmetric Synthesis of (+)-2-epi-α-Allokainic Acid Employing Ketopinic Amide as Chiral Auxiliary

Authors

廖得仲

Key Words

紅藻胺酸 ; 樟腦 ; 樟腦黃醯胺 ; 輔助基 ; 不對稱合成 ; 1,4-加成 ; 不對稱1,4-加成 ; 不對稱麥克加成 ; Asymmetric Synthesis ; (+)-2-epi-α-Allokainic Acid ; Ketopinic Amide ; Chiral Auxiliary ; Michael reaction ; Asymmetric Michael reaction

PublicationName

清華大學化學系所學位論文

Volume or Term/Year and Month of Publication

2015年

Academic Degree Category

碩士

Advisor

汪炳鈞

Content Language

繁體中文

Chinese Abstract

本論文利用樟腦醯胺139作為掌性輔助基,與甘胺酸第三丁酯142縮合形成之樟腦醯基亞胺116為起始物,經由1,4-加成反應建構立體中心得到單一非鏡像異構物之加成物130;隨後利用胺轉換法將掌性輔助基水解並進行合環反應,合成內醯胺(lactam)結構的焦谷胺酯(pyroglutamate) 147,最後以羥醛反應建構出C4位置具有不對稱中心的紅藻胺酸前驅物157,藉此合成C2-epi-紅藻胺酸 (+)-2-epi-α-Allokainic acid 128。

English Abstract

This thesis deals with the application of camphor-derived ketopinic amide 139 as a chiral auxiliary in the synthesis of pyrrolidine alkaloids. Asymmetric 1,4-addition of chiral imine 116, derived from glycinate 142 and ketopinic amide 139, with α,β-unsaturated ester 142 afforded adduct 130 as a single isomer. Transamination of compound 130, followed by cyclization provided lactam 147. The construction of C4 stereogenic center was achieved by the aldol reaction of boc-protected lactam 147 with acetone. Further functional group transformation led to the synthesis of (+)-2- epi-α-Allokainic acid 128.

Topic Category 基礎與應用科學 > 化學
理學院 > 化學系所
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