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
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2019
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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.
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.
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有機連鎖反應, 丙烯基醋酸酯, 四氫呋喃苯并吡喃, domino reaction, nitroallylic acetate, tetrahydrofurano benzopyrans