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Preparative Monomethylation of 2,3,5,6,7,8-Hexahydroxynaphthalene-1,4-dione (Spinochrome E). The First Direct Synthesis of Namakochrome: the Natural Pigment of the Holothurian Polycheira rufescens

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Abstract

A 4-step preparative conversion of the available sea urchins pigment spinochrome E into the holothurian Polycheira rufescens pigment namakochrome was developed. Spinochrome E was converted into hexaacetate, and one β-acetate group in the quinone core of the latter was selectively removed. The resulting pentaacetate was treated with diazomethane, and all protective acetate groups were removed by treatment with methanolic HCl. The total yield of namakochrome over 4 steps was ~46–51%.

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ACKNOWLEDGMENTS

The authors are grateful to Cand. Sci. (Phys.-Math.) V.P. Glazunov for recording the IR spectra.

Funding

The work was financially supported by the Russian Science Foundation (project no. 19-14-00047).

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Authors and Affiliations

  1. G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, 690022, Vladivostok, Russia

    S. G. Polonik, V. A. Denisenko, R. S. Popov, A. A. Artjukov & Y. E. Sabutskii

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  1. S. G. Polonik
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  2. V. A. Denisenko
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  3. R. S. Popov
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  4. A. A. Artjukov
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  5. Y. E. Sabutskii
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Correspondence to S. G. Polonik.

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Polonik, S.G., Denisenko, V.A., Popov, R.S. et al. Preparative Monomethylation of 2,3,5,6,7,8-Hexahydroxynaphthalene-1,4-dione (Spinochrome E). The First Direct Synthesis of Namakochrome: the Natural Pigment of the Holothurian Polycheira rufescens. Russ J Org Chem 56, 207–212 (2020). https://doi.org/10.1134/S1070428020020050

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