通过新型氧化自由基反应便捷合成九里香醌A
An Expedient Synthesis of Murrayaquinone A via a Novel Oxidative Free Radical Reaction.
作者信息
McDonald Jeffrey W, Miller John E, Kim Minjee, Velu Sadanandan E
机构信息
Department of Chemistry, University of Alabama at Birmingham, 901 14th Street South, Birmingham, AL 35294-1240, USA.
Comprehensive Cancer Center, University of Alabama at Birmingham, 1720 2nd Avenue South, Birmingham, AL 35294-3300, USA.
出版信息
Tetrahedron Lett. 2018 Feb 7;59(6):550-553. doi: 10.1016/j.tetlet.2018.01.007. Epub 2018 Jan 4.
Abstract
Murrayaquinones A-D is a group of four bioactive carbazole-1,4-dione natural products isolated from the root bark of the plant hayata. Murrayaquinone is synthesized in five steps starting from the commercially available 2,4,5-trimethoxybenzaldehyde with an overall yield of 45%. The novelty of this murrayaquinone synthesis is in the use of a Mn(OAc) mediated oxidative radical reaction of a N-benzylaminoquinone derivative with 2-cyclohexen-1-one for the late-stage indole ring construction.
摘要
九里香醌A - D是从植物早田氏（Murraya hayata）根皮中分离出的一组四种具有生物活性的咔唑 - 1,4 - 二酮天然产物。九里香醌以市售的2,4,5 - 三甲氧基苯甲醛为起始原料，经五步合成，总产率为45%。这种九里香醌合成方法的新颖之处在于使用了醋酸锰介导的N - 苄基氨基醌衍生物与2 - 环己烯 - 1 - 酮的氧化自由基反应来进行后期吲哚环的构建。
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