Total Synthesis of (�)-Panduratin D

Please use this identifier to cite or link to this item: http://ir.lib.ncu.edu.tw/handle/987654321/66764

Title:	Total Synthesis of (�)-Panduratin D
Authors:	趙翊豪;Chao,I-hao
Contributors:	化學學系
Keywords:	狄耳士-阿德爾反應;羥基定向烷化反應;panduratin D;Diels-Alder reaction;hydroxyl-directed alkylation
Date:	2015-01-30
Issue Date:	2015-03-16 15:10:57 (UTC+8)
Publisher:	國立中央大學
Abstract:	從凹唇薑(或稱高良薑)身上萃取出的(–)-panduratin D被檢驗在營養喪失的條件下，有些許抗人類胰腺癌細胞活性，然而至今沒有關於(–)-panduratin D的全合成文獻發表。我們以3-甲氧苯酚作為起始物，經由10步合成成功得到外消旋panduratin D。關鍵步驟包含使用鄰位陰離子夫裏士重排(anionic ortho-Fries rearrangement)及薗頭耦合合環(Sonogashira coupling annulation)反應來建構苯并呋喃的本體結構、鄰位定向硼酸鹽氧化反應、醯胺的烷化反應、醛醇縮合作用，以及最後在狄耳士-阿德爾反應後建立此化合物的立體中心。確定路徑後，我們在最後一步嘗試做狄耳士-阿德爾的不對稱反應來得到單一的鏡像異構物；我們也嘗試做羥基定向烷化反應取代親核性烷基鋰試劑的使用。;(–)-panduratin D, isolated from Boesenbergia pandurate, was examined a mild activity against human pancreatic PANC-1 cancer cells under nutrient-deprived conditions. We first synthesized racemic panduratin D from 3-methoxyphenol in 10 steps. The key features included construction of benzofuran system by anionic ortho-Fries rearrangement and Sonogashira coupling annulation of 2-iodo-3-methoxyphenyl diethylcarbamate, directed ortho borate oxidation, alkylation of amide, aldol condensation, as well as Diels-Alder reaction, which established the stereocenter. Later, we tried some enantioselective Diels-Alder reactions expected to afford single enantiomer; we also tried applying hydroxyl-directed alkylation in place of alkylation with nucleophilic alkyl lithium reagent.
Appears in Collections:	[Graduate Institute of Chemistry] Electronic Thesis & Dissertation

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