An expedient synthesis of murrayaquinone A via a novel oxidative free radical reaction. Issue 6 (7th February 2018)

• Record Type: Journal Article
• Authors: McDonald, Jeffrey W.; Miller, John E.; Kim, Minjee; Velu, Sadanandan E.
• Is Part Of: Tetrahedron letters. Volume 59:Issue 6(2018)
• Page Start: 550
• Page End: 553
• Publication Date: 2018-02-07
• Subjects: Natural product -- Synthesis -- Murrayaquinone -- Oxidative -- Radical; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.01.007
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Murrayaquinone A is synthesized in five steps in an overall yield of 45%. The synthesis uses of a novel Mn(OAc)3 mediated oxidative radical reaction. It differs from the existing methods in the late-stage indole ring construction. This methodology provides rapid synthetic access to carbazole-1, 4-diones. 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.