Synthesis ( IF 2.2 ) Pub Date : 2018-11-21 , DOI: 10.1055/s-0037-161114 Leslie Aldrich 1 , Qiwen Gao , Lianyan Xu , Vincent Parise , Yash Mehta
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Abstract
A concise method that is easily amenable for analogue synthesis has been developed to enantioselectively access 4-amino-3-hydroxybenzopyrans from chalcones. Epoxy alcohols were formed from chalcones through a Corey–Bakshi–Shibata reduction of the enone and subsequent Sharpless asymmetric epoxidation of the allylic alcohol. The epoxy alcohols were protected, regioselectively opened with various amines using catalytic europium(III) triflate, and the resulting free alcohols were orthogonally protected. Concomitant deprotection and intramolecular nucleophilic aromatic substitution provided the benzopyran core, which is poised to undergo additional reactions to provide a diverse chemical library with ideal properties for biological evaluation.
A concise method that is easily amenable for analogue synthesis has been developed to enantioselectively access 4-amino-3-hydroxybenzopyrans from chalcones. Epoxy alcohols were formed from chalcones through a Corey–Bakshi–Shibata reduction of the enone and subsequent Sharpless asymmetric epoxidation of the allylic alcohol. The epoxy alcohols were protected, regioselectively opened with various amines using catalytic europium(III) triflate, and the resulting free alcohols were orthogonally protected. Concomitant deprotection and intramolecular nucleophilic aromatic substitution provided the benzopyran core, which is poised to undergo additional reactions to provide a diverse chemical library with ideal properties for biological evaluation.
中文翻译：
查尔酮类化合物的对映选择性合成4-氨基-3-羟基苯并吡喃黄酮衍生物
摘要
已经开发出一种易于进行类似物合成的简明方法，以对映选择性地从查耳酮中获得4-氨基-3-羟基苯并吡喃。查耳酮通过Corey-Bakshi-Shibata还原烯酮并随后使烯丙醇进行Sharpless不对称环氧化反应而形成环氧醇。保护环氧醇，使用催化三氟甲磺酸catalytic（III）用各种胺区域选择性地打开，并将得到的游离醇正交保护。伴随的脱保护和分子内亲核芳族取代提供了苯并吡喃核，该苯并吡喃核准备进行额外的反应以提供具有理想性质的多种化学文库用于生物学评估。
已经开发出一种易于进行类似物合成的简明方法，以对映选择性地从查耳酮中获得4-氨基-3-羟基苯并吡喃。查耳酮通过Corey-Bakshi-Shibata还原烯酮并随后使烯丙醇进行Sharpless不对称环氧化反应而形成环氧醇。保护环氧醇，使用催化三氟甲磺酸catalytic（III）用各种胺区域选择性地打开，并将得到的游离醇正交保护。伴随的脱保护和分子内亲核芳族取代提供了苯并吡喃核，该苯并吡喃核准备进行额外的反应以提供具有理想性质的多种化学文库用于生物学评估。
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