氧化呋喃-吲哚重排。2-(2-酰基乙烯基)吲哚和 Flinderole C 类似物的合成。
Oxidative Furan-to-Indole Rearrangement. Synthesis of 2-(2-Acylvinyl)indoles and Flinderole C Analogues.
机构信息
Department of Chemistry, Perm State University , Bukireva st. 15, Perm 614990, Russia.
Institute of Technical Chemistry UrB RAS, Academika Koroleva st. 3, Perm 614013, Russia.
出版信息
Org Lett. 2016 May 6;18(9):2192-5. doi: 10.1021/acs.orglett.6b00805. Epub 2016 Apr 13.
Oxidative rearrangement of 2-(2-aminobenzyl)furans affording 2-(2-acylvinyl)indoles in a stereocontrolled manner in good-to-excellent yields has been developed. Thus, (2-aminobenzyl)furans with electron-releasing alkoxy substituents in the phenyl group form only E-isomers of 2-(2-acylvinyl)indoles. Conversely, substrates without such substituents produce target products as Z-isomers exclusively. A short diastereoselective method for the transformation of the obtained 2-(2-acylvinyl)indoles into antimalarial bisindole alkaloid flinderole A-C analogues has been developed.
已经开发出一种通过氧化重排 2-(2-氨基苄基)呋喃，以良好至优异的收率立体控制方式得到 2-(2-酰基乙烯基)吲哚的方法。因此，苯环上带有给电子烷氧基取代基的(2-氨基苄基)呋喃仅形成 2-(2-酰基乙烯基)吲哚的 E-异构体。相反，没有此类取代基的底物则以 Z-异构体为唯一产物。开发了一种短的非对映选择性方法，用于将获得的 2-(2-酰基乙烯基)吲哚转化为抗疟双吲哚生物碱 flinderole A-C 类似物。
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