Chemistry of Natural Compounds

, Volume 52, Issue 2, pp 213–217 | Cite as

Synthesis of Spinochrome D, A Metabolite of Various Sea-Urchin Species

  • N. N. Balaneva
  • O. P. Shestak
  • V. F. Anufriev
  • V. L. Novikov
Article
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The sea-urchin metabolite spinochrome D (1) was synthesized in 58% overall yield via oxidation of 2,3-dichloronaphthazarin (13) into 2-hydroxy-6,7-dichloronaphthazarin (14), O-methylation of 14, nucleophilic substitution by MeO groups of the Cl atoms in the resulting 2-methoxy-6,7-dichloronaphthazarin (19), and hydrolysis of the obtained 2,3,6-trimethoxynaphthazarin (10).

Keywords

sea-urchin metabolites polyhydroxy-1,4-naphthoquinones naphthazarins spinochrome D oxidation O-alkylation nucleophilic substitution antioxidants 
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Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  • N. N. Balaneva
    • 1
  • O. P. Shestak
    • 1
  • V. F. Anufriev
    • 1
  • V. L. Novikov
    • 1
  1. 1.G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-East BranchRussian Academy of SciencesVladivostokRussian Federation

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