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An Expedient Synthesis of Murrayaquinone A via a Novel Oxidative Free Radical Reaction.

ABSTRACT: 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.

SUBMITTER: McDonald JW

PROVIDER: S-EPMC5935454 | biostudies-literature | 2018 Feb

REPOSITORIES: biostudies-literature

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An Expedient Synthesis of Murrayaquinone A via a Novel Oxidative Free Radical Reaction.

McDonald Jeffrey W JW Miller John E JE Kim Minjee M Velu Sadanandan E SE

Tetrahedron letters 20180104 6

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 lat ...[more]

PMID: 29736091

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