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

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 result...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2020-04, Vol.56 (2), p.207-212
Main Authors: Polonik, S. G., Denisenko, V. A., Popov, R. S., Artjukov, A. A., Sabutskii, Y. E.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Diazomethane
Organic Chemistry
Quinones
Sea urchins
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Summary: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%.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428020020050