噁唑烷酮稠合吖環丙烷進行羥基開環反應與KRN7000環己醇類似物之合成研究;Hydroxyl Group Ring-Opening of Oxazolidinone Fused Aziridine and Synthesis of KRN7000 analogue

Please use this identifier to cite or link to this item: http://ir.lib.ncu.edu.tw/handle/987654321/89242

Title:	噁唑烷酮稠合吖環丙烷進行羥基開環反應與KRN7000環己醇類似物之合成研究;Hydroxyl Group Ring-Opening of Oxazolidinone Fused Aziridine and Synthesis of KRN7000 analogue
Authors:	吳勁勳;Wu, Chin-Hsun
Contributors:	化學學系
Keywords:	噁唑烷酮稠合吖環丙烷;羥基開環反應;肌醇衍生物
Date:	2022-09-29
Issue Date:	2022-10-04 11:02:21 (UTC+8)
Publisher:	國立中央大學
Abstract:	本論文的目標為合成KRN7000衍生物。以對稱雙烯醇為起始物進行夏普萊斯不對稱環氧化反應 (Sharpless asymmetric epoxidation) 生成含有兩個立體中心的環氧化合物，再利用十二烷基格林納試劑 (Grignard reagent) 對其進行開環反應延伸碳鏈。接著以高效率微波加熱的方式進行吖環丙烷化反應 (stereoselective aziridination) 建立第三個立體中心並具良好的非鏡像選擇性。其關鍵步驟是以肌醇衍生物對吖環丙烷進行開環反應生成碳氧鍵。最後經由數步反應得到目標產物。;Sharpless asymmetric epoxidation was carried out with a symmetric dienol as the starting material to generate a chiral epoxide containing two stereocenters. The carbon chain was elongated by the ring-opening reaction with dodecyl Grignard reagent. The third stereocenter is established by a diastereoselective aziridination reaction, assisted with highly-efficient microwave heating. The most critical step is to conduct the aziridine ring-opening reaction with an inositol derivative to generate the carbon-oxygen bond, and then obtain the target product KRN7000 derivative through several transformations.
Appears in Collections:	[Graduate Institute of Chemistry] Electronic Thesis & Dissertation

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