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Title: 三乙基胺促進連鎖反應合成多取代四氫呋喃苯并吡喃之架構
Amine-Promoted Domino Reaction: Construction of Multi-Substituted Tetrahydrofurano Benzopyrans
Authors: 陳焜銘
Wu, Yu-Chen
Keywords: 有機連鎖反應
domino reaction
nitroallylic acetate
tetrahydrofurano benzopyrans
Issue Date: 2019
Abstract: 近幾年來,已經發現具有四氫呋喃苯并吡喃架構的天然物,甚至有些天然物擁有生物活性。目前探討合成此類架構的文獻相對稀少,本文提供新的合成途徑,藉由有機鹼三乙基胺,促進具有多親電位子的硝基丙烯基醋酸酯,與多親核位子的1-(2’-羥基苯基)丁烷-1,3-二酮,在低溫的條件下,進行高效率的連鎖反應Michael/acetalization/oxa-Michael反應,合成三環並聯線性的外消旋多取代四氫呋喃苯并吡喃,其架構具有四個連續的立體中心,包含兩個四級碳立體中心,產率可達62%。在反應選擇性方面,多取代四氫呋喃苯并吡喃與多取代呋喃比例為5:1-6:1。不對稱合成高純光學純度之呋喃苯并吡喃產物,後續在研究探討。
In recent years, the tetrahydrofurano benzopyrans had been found from nature, some of which were bioactive. There was little literature on synthesis of these scaffolds. A new and convenient method for triethyl amine to promote effective domino reaction (Michael/acetalization/oxa-Michael reaction) of electrophilic nitroallylic acetate and nucleophilic 1-(2’-hydroxyphenyl)butane-1,3-dione. It was carried out under low temperature to synthesize racemic multi-substituted tetrahydrofurano benzopyrans bearing consecutive four stereogenic centers in moderate yield. And chemoselectivities was good (tetrahydrofurano benzopyrans : furan = 5:1-6:1). However, our efforts will focus on asymmetric synthesis of product in the future.
Other Identifiers: G060642059S
Appears in Collections:學位論文

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