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Simple preparative synthesis of spinochrome e, a pigment from sea urchins of the genus Echinothrix

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Chemistry of Natural Compounds Aims and scope

A preparative synthesis of spinochrome E (2,3,5,6,7,8-hexahydroxy-1,4-naphthoquinone, 1), a metabolite of sea urchins of the genus Echinothrix, is proposed starting from 2,3-dichloro-6,7-diethoxynaphthazarine (4) with simultaneous substitution of the Cl atoms by hydroxyl- and nitro-groups, reduction of the latter, and subsequent removal of alkoxy groups and hydrolysis of the amine in the resulting 3-amino-2-hydroxy-6,7-diethoxynaphthazarine (6).

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Notes

  1. Structures of naphthazarine derivatives are given only for one of all possible tautomers.

References

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Acknowledgment

The work was supported financially partially by a grant of the RAS Presidium (Molecular and Cellular Biology Program) and an Interdisciplinary Integrated Project of the Far-East, Siberian, and Ural Branches of the RAS (No. 09-11-SB-05-001).

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Authors and Affiliations

  1. G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-East Branch, Russian Academy of Sciences, 690022, Vladivostok, Prosp. 100-Letiya Vladivostoka, 159, Russian Federation

    K. L. Borisova & V. F. Anufriev

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  1. K. L. Borisova
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  2. V. F. Anufriev
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Correspondence to V. F. Anufriev.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 2, March–April, 2012, pp. 187–189.

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Borisova, K.L., Anufriev, V.F. Simple preparative synthesis of spinochrome e, a pigment from sea urchins of the genus Echinothrix . Chem Nat Compd 48, 202–204 (2012). https://doi.org/10.1007/s10600-012-0204-6

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