An expedient synthesis of murrayaquinone A via a novel oxidative free radical reaction

TETRAHEDRON LETTERS

卷:59

Article

McDonald, Jeffrey W.¹  Miller, John E.¹  Kim, Minjee¹  Velu, Sadanandan E.^1,2 

[1] Univ Alabama Birmingham, Dept Chem, 901 14th St South, Birmingham, AL 35294 USA

[2] Univ Alabama Birmingham, Ctr Comprehens Canc, 1720 2nd Ave South, Birmingham, AL 35294 USA

关键词: Natural product;    Synthesis;    Murrayaquinone;    Oxidative;    Radical;   

DOI  :  10.1016/j.tetlet.2018.01.007

来源: Elsevier

【 摘 要 】

Murrayaquinones A-D is a group of four bioactive carbazole-1,4-dione natural products isolated from the root bark of the plant Murraya eucrestifolia 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)(3) mediated oxidative radical reaction of a N-benzylaminoquinone derivative with 2-cyclohexen-1-one for the late-stage indole ring construction. (C) 2018 Elsevier Ltd. All rights reserved.

【 授权许可】

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