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研究生:張惠婷
研究生(外文):Hui-Ting Chang
論文名稱:不對稱全合成(-)-Pericosine A 及探索(-)-Pericosine C 的合成路徑
論文名稱(外文):Asymmetric Total Synthesis of (-)-Pericosine A and Synthetic Studies toward (-)-Pericosine C
指導教授:楊圖信
指導教授(外文):Tu-Hsin Yan
口試委員:李衍彰楊定亞
口試日期:2014-07-25
學位類別:碩士
校院名稱:國立中興大學
系所名稱:化學系所
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:2014
畢業學年度:102
語文別:英文
論文頁數:131
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This thesis we described the asymmetric synthesis of (-)-Pericosine A and C. Starting from commercial available C2-symmetrical L-tartaric acid, the target molecules could be accomplished within a short path. Critical to the fulfillment of this work was 1,4-conjugate addition of cyanide reaction and the utilization of alcoholysis to the transformation from cyano moiety to carboxylic ester.

List of schemes………I
List of figures………II
List of tables………III
Abbreviation………. IV
Preface………Ⅶ
Chapter 1 Introduction………1
1.1 Structures and biological activities of carbasugars………1
1.2 Pericosine family and biological activities………2
Chapter 2 Asymmetric total synthesis of (-)-Pericosine A………4
2.1 Review of past synthesis for Pericosine A………4
2.2 Retrosynthetic analysis of (-)-Pericosine A………11
2.3 Result and discussion………12
2.3.1 Attempt to construct the main core of cyclohexenediol 6………12
2.3.2 Solvent effect in our case of ring-closing metathesis (RCM) ………13
2.3.3 Synthesis of allyl epoxide 5 as pivotal intermediate………15
2.3.4 Highly regio and stereo selectivity in the formation of hydrochlorin 10………15
2.3.5 One pot reaction of TFA-promoted isomerization followed by Dess-Martin oxidation………..17
2.3.6 Strategies to install the final carbon on C (1) of (-)-Pericosine A………18
2.3.7 Chemo and stereo selective reduction………25
2.3.8 Hydrolysis of cyano group to reach the total synthesis of (-)-Pericosine A……27
Chapter 3 Synthetic studies toward (-)-Pericosine C……29
3.1 Review of past synthesis for Pericosine C……29
3.2 Retrosynthetic analysis of (-)-Pericosine C……33
3.3Result and discussion……34
3.3.1 Exploration to the SN2-type ring-opening of allyl epoxide 5……34
3.3.2 Trapping the formation TFA-promoted isomer 29……37
3.3.3 Synthesis of α,β-unsatured ketone 26 as precursor for 1,4-addition……38
Chapter 4 Conclusion……40
Chapter 5 Future work……41
Chapter 6 Experimental section……42
6.1 General experiments……42
6.2 Instruments……42
6.3 Procedure and characterization……44
Chapter 7 References……56
Appendix :Spectra data

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