Title page for 972203028


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Student Number 972203028
Author Chun-yi Wang(王淳逸)
Author's Email Address No Public.
Statistics This thesis had been viewed 467 times. Download 212 times.
Department Chemistry
Year 2010
Semester 1
Degree Master
Type of Document Master's Thesis
Language zh-TW.Big5 Chinese
Title Total synthesis of (+)-Aspicilin
Date of Defense 2010-09-27
Page Count 127
Keyword
  • aspicilin
  • esterification
  • RCM
  • Ring crossing metathesis
  • total synthesis
  • Abstract (+)-Aspicilin was synthesized using (3R,4R)-hexa-1,5-diene-3,4-diol as the starting material. We applied Sharpless epoxidation to create the third chirality center. Diethyl malonate was used to attack the epoxide to produce lactone, which was hydrolyzed to give acid. Esterification of acid and (S)-dodec-11-en-2-ol was achieved by Yamaguchi esterification. Ring cross metathesis (RCM) was applied to give the 18-membered ring macrolactone. The synthesis of (+)-aspicilin was completed by hydrogenation, selenylation, oxidation, and deprotection.
    Table of Content 中文摘要.............................................I
    英文摘要.............................................II
    致謝................................................ III
    總目錄.............................................. IV
    流程圖目錄.......................................... VI
    圖目錄...............................................VII
    表格目錄.............................................VIII
    方程式目錄...........................................IX
    附圖目錄.............................................XI
    第一章 前言.........................................1
    1-1  利用Photolactonization合環,合成天然物(+)-Aspicilin............................................2
    1-2  利用Yamaguchi esterification合成天然物(+)-Aspicilin............................................4
    1-3  利用allylation與Yamaguchi esterification合成天然物(+)-Aspicilin........................................6
    1-4  利用環閉合置換反應(RCM)合成天然物(+)-Aspicilin............................................9
    1-5  利用allylation與環閉合置換反應(RCM)合成天然物(+)-Aspicilin............................................12
    1-6  利用Wadsworth-Emmons reaction合成天然物(+)-Aspicilin............................................15
    1-7  烯烴置換(olefin metathesis)反應的發展史概論....17
    1-8  高效能催化劑的問世.............................22
    1-9  烯烴置換反應類型...............................25
    第二章  結果與討論..................................28
    2-1  逆合成分析.....................................28
    2-2  起始物合成.....................................30
    2-3  (+)-Aspicilin的合成............................31
    2-4  路徑A的測試....................................33
    2-5  路徑B的測試....................................37
    第三章  結論........................................42
    第四章  實驗........................................43
    4-1  溶媒及處理過程.................................43
    4-2  實驗器材與儀器...................................................43
    4-3  實驗步驟.......................................45
    第五章  參考文獻....................................66
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    Advisor
  • Duen-Ren Hou(侯敦仁)
  • Files
  • 972203028.pdf
  • approve in 2 years
    Date of Submission 2010-09-29

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