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).
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Translated from Khimiya Prirodnykh Soedinenii, No. 2, March–April, 2016, pp. 187–191.
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Balaneva, N.N., Shestak, O.P., Anufriev, V.F. et al. Synthesis of Spinochrome D, A Metabolite of Various Sea-Urchin Species. Chem Nat Compd 52, 213–217 (2016). https://doi.org/10.1007/s10600-016-1597-4
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DOI: https://doi.org/10.1007/s10600-016-1597-4