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研究生:林士哲
研究生(外文):Shih-Che Lin
論文名稱:從香葉醇到二萜類天然物Galanal A和Galanal B之全合成
論文名稱(外文):Total Synthesis of the Labdane Diterpenes Galanal A and Galanal B from Geraniol
指導教授:陳榮傑陳榮傑引用關係鄭原忠
指導教授(外文):Rong-Jie CheinYuan-Chung Cheng
口試日期:2017-07-25
學位類別:博士
校院名稱:國立臺灣大學
系所名稱:化學研究所
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2017
畢業學年度:105
語文別:英文
論文頁數:247
中文關鍵詞:二萜類天然物多烯環化反應鈦陽離子自由基環化反應
外文關鍵詞:galanal Agalanal Bpolyene cyclizationtitanocene radical cyclization
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本論文的第一章節由天然物galanal A和B的第一個全合成研究所構成,合成路徑從自然界中含量豐富的香葉醇原料開始。關鍵步驟分別是路易士酸輔助手性布忍斯特酸複合體所調控的陽離子多烯環化反應以及鈦陽離子調控的自由基環化反應分別來建構不對稱的AB雙環結構以及在BC雙環連接點位置上的全碳原子連結之四級碳原子中心。
本論文的第二章節由不對稱多烯環化反應的文獻回顧以及將氫原子引發的不對稱多烯環化反應用在galanal A和B全合成路徑中的雙烯基質之研究探討所組成。經過配位基和路易士酸的篩選之後,R型苄基單取代聯萘酚與四氯化錫所組成的路易士酸輔助手性布忍斯特酸複合體組合,將其應用在雙烯基質上,給予我們最高的鏡像異構物超越值。後續有關提升鏡像異構物超越值的相關研究仍在進行中。
The first chapter of this dissertation concerns the first total synthesis of galanal A and B, which has been achieved from naturally occurring geraniol. Key steps in this synthesis are the use of a Lewis acid assisted chiral Brønsted acid (chiral LBA) mediated cationic polyene cyclization and a titanocene-mediated radical cyclization for the asymmetric assembly of the “AB” ring and the construction of the all-carbon quaternary center at the “BC” ring junction, respectively.
The second chapter of this dissertation comprises of the literature review of enantioselective polyene cyclizations and studies of a proton-initiated enantioselective polyene cyclization, applied to the diene substrate in the total synthesis of galanal A and B. Screening of ligands and Lewis acids gave us (R)-BINOL-Bn and SnCl4 as, the chiral LBA pair that gives us the highest ee of our substrate. Further improvement of ee is under investigation.
Abstract..........................................ii
中文摘要…………...............................iv
謝誌……………….................................vi
List of Abbreviations......................viii
Table of Contents............................x
List of Schemes............................xiv
List of Figures..............................xvii
List of Tables................................xix
Chapter 1. Total Synthesis of Galanal A and Galanal B 1
1.1 Introduction 1
1.1.1 Incretins and Type-2 Diabetes 1
1.1.2 GLP-1 Receptor Agonist (GLP-1RA) 2
1.1.3 DPP4-inhibitors 6
1.1.4 Properties of GLP-1RAs and DPP4-inhibitors 7
1.1.5 Motivation for Searching Positive Modulators and the Endocytosis Bioassay 8
1.1.6 The Major Active Compound in Ginger Lily 11
1.1.7 Literature Survey 13
1.2 Results and discussion 17
1.2.1 Retrosynthetic analysis of galanal A and B 17
1.2.2 Synthesis of Compound 5 18
1.2.3 Trials for Construction of the All-carbon Quaternary of 4 24
1.2.4 Trials of the Following Steps in Retrosynthetic Analysis 28
1.2.5 Revised Retrosynthetic Analysis of Galanal A and B 31
1.2.6 Baeyer-Villiger Reaction Studies 33
1.2.7 Optimization of the Reaction Conditions for the Synthesis of Ketone 5 36
1.2.8 Biomimetic Synthetic Strategy toward the Synthesis of Galanal A and B 37
1.2.9 Ring-opening of Lactone 28 and Synthesis of Epoxyester 38
1.2.10 Synthesis of the Epoxynitrile 38 43
1.2.11 Construction of the All−carbon Quaternary Center at the “BC” Ring Junction 44
1.2.12 Studies Toward Compound 41 46
1.2.13 Synthesis of Galanal A and B from 35 48
1.2.14 DFT Calculations of Compound 44 and 45 51
1.2.15 Galanal B Positively Modulates GLP-1 Receptor Signaling 56
1.2.16 Oral Glucose Tolerance Test on Lean Mice 57
1.3 Conclusion 58
Chapter 2. Studies of Enantioselective Polyene Cyclization 59
2.1 Introduction 59
2.1.1 Polyene Substrate Bearing a Prenyl Terminal Group 59
2.1.2 Polyene Substrate Bearing a Non-prenyl Terminal group 67
2.2 Results and Discussion 75
2.2.1 Trials of Literature Report of Enantioselective Proton-Initiated Polyene Cyclization 75
2.2.2 Polyene Cyclization Lewis Acid Screening 78
2.2.3 Polyene Cyclization with other Types of Ligand Screening 80
2.2.4 Polyene Cyclization with BINOL-related Ligand Screening 83
2.2.5 Polyene Cyclization with Helicenol-like Ligand 85
2.3 Conclusion 86
Chapter 3. Experimental Section 87
3.1 General Method 87
3.2 Experimental Procedures and Spectra Data 88
3.3 Optimized Geometries of compound 44 and 45 135
References 171
Appendix 176
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