三取代的吖環丙烷進行開環反應生成碳立體中心研究

Please use this identifier to cite or link to this item: http://ir.lib.ncu.edu.tw/handle/987654321/80439

Title:	三取代的吖環丙烷進行開環反應生成碳立體中心研究
Authors:	劉淇云;LIU, CHI-YUN
Contributors:	化學學系
Keywords:	吖環丙烷;掌性四級碳中心;非鏡像選擇性;ent-Kijanoside
Date:	2019-08-22
Issue Date:	2019-09-03 14:31:49 (UTC+8)
Publisher:	國立中央大學
Abstract:	中文摘要本論文以 ethyl L-lactate 作為起始物，經由多步驟反應，分別合成 Z 型和 E 型烯類化合物 (6 E、16 Z、24 Z)，再以此烯類化合物生成4-甲基-3-氧-1-氮二環[3.1.0]己烷-2-酮 (4-methyl-3-oxa-1-azabicyclo[3.1.0] hexan-2-one) (11、19、27)，再以4-甲基-3-氧-1-氮二環[3.1.0]己烷-2-酮與親核試劑，進行親核加成反應，形成單一鏡像化合物 (enantiopure compounds)，以建構具有掌性的四級碳中心。最後，將此策略應於合成ent-D-Kijanose 31 a/b。由於 D-Kijanose 為一具有支鏈的特殊硝基醣 (nitrosuga)，而該硝基醣與已知具有生物活性的 kijanimicin 結合後，將擁有良好的抗腫瘤性和抗生素的活性，因此合成 ent-Kijanoside 為本論文致力研究的目標產物。關鍵字：吖環丙烷，掌性四級碳中心，非鏡像選擇性，ent-Kijanoside ;Abstract In this paper, ethyl L-lactate was used as a starting material to synthesize Z-type and E-type alkenes (6 E、16 Z、24 Z) through a multi-step reaction, respectively. The compounds synthesize 4-methyl-3-oxa-1-azabicyclo[3.1.0] hexan-2-one (11、19、27), followed by a 4-methyl-3-oxa-1-azabicyclo[3.1.0] hexan-2-one is subjected to a nucleophilic addition reaction with a nucleophile to form a single diastereoisomer to construct a chiral quaternary carbon center. Finally, the method of constructing a chiral quaternary carbon center was applied to ent-D-Kijanose′s synthesis strategy. Since D-Kijanose is a branched nitrosuga, which connects with the biologically active Kijanimicin, it has antitumor and antibiotic activity.Therefore, the synthesis of ent-Kijanoside is the target product of this paper. Keywords: aziridine, chiral quaternary carbon center, diastereoselectivity, ent-Kijanoside.
Appears in Collections:	[Graduate Institute of Chemistry] Electronic Thesis & Dissertation

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