置換（Metathesis）反應合成(+)-Cladospolide C

Please use this identifier to cite or link to this item: http://ir.lib.ncu.edu.tw/handle/987654321/6194

Title:	置換（Metathesis）反應合成(+)-Cladospolide C
Authors:	周君易;Chun-Yi Chou
Contributors:	化學研究所
Keywords:	置換（Metathesis）;Metathesis;Cladospolide C
Date:	2005-07-05
Issue Date:	2009-09-22 10:15:18 (UTC+8)
Publisher:	國立中央大學圖書館
Abstract:	我們採用化合物35當作起始物來合成(+)-Cladospolide C。起始物先與丙烯醯甲酯進橫跨置換反應的到了一次橫跨置換的產物，此產物接著與(R)-庚-6-烯-2-醇進行二次橫跨置換反應以導入第三個立體中心。然後，將此二次橫跨置換產物氫化以還原雙鍵，接著水解甲酯得到酸。緊接著以Yamaguchi內酯化反應為合環步驟得到十二員環的內酯。以二異丙胺鋰拔掉內酯的α位置氫來與苯硒官能基烷化、接著用過氧化氫氧化此分子重新生成共軛雙鍵，得到(+)-Cladospolide C。 (+)-Cladospolide C was synthesized using diene 35 as a the strating material. Two consecutive cross metatheses (CM) reactions of 35 and methyl acrylate, then (R)-hept-6-en-2-ol provided the carbon skeleton with the required stereochemistry. The double CM product was hydrogenated, followed by hydrolysis to give the acid. Yamaguchi lactonization was used to form the lactone with twelve-membered ring. The synthsis of (+)-Cladospolide C was completed by regenerating the α, β-unsaturated lactone using selenylation, oxidation, and deprotection.
Appears in Collections:	[Graduate Institute of Chemistry] Electronic Thesis & Dissertation

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