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

Tetrahedron Lett

Department of Chemistry, University of Alabama at Birmingham, 901 14th Street South, Birmingham, AL 35294-1240, USA.

Published: February 2018

AI Article Synopsis

  • Murrayaquinones A-D are four bioactive compounds derived from the root bark of the plant Hayata.
  • The synthesis of Murrayaquinone involves five steps starting from 2,4,5-trimethoxybenzaldehyde, achieving a total yield of 45%.
  • A key innovation in this synthesis is the use of a manganese acetate-mediated oxidative radical reaction to help form the indole ring in the final stages.

Article 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.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5935454PMC
http://dx.doi.org/10.1016/j.tetlet.2018.01.007DOI Listing

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