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Synthesis 2016; 48(05): 761-764
DOI: 10.1055/s-0035-1560389
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of Mirabiquinone A: A Biquinone from the Sea Urchin Scaphechinus mirabilis and Related Compounds

Dmitry N. Pelageev
a   G. B. Elaykov Pacific Institute of Bioorganic Chemistry FEB RAS, Prospect 100 let Vladivostoku 159, 690022 Vladivostok, Russian Federation   Email: anufriev@piboc.dvo.ru
b   School of Natural Sciences, Far East Federal University, Sukhanova St. 8, 690950 Vladivostok, Russian Federation
,
Victor Ph. Anufriev*
a   G. B. Elaykov Pacific Institute of Bioorganic Chemistry FEB RAS, Prospect 100 let Vladivostoku 159, 690022 Vladivostok, Russian Federation   Email: anufriev@piboc.dvo.ru
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Publication History

Received: 30 September 2015

Accepted after revision: 20 November 2015

Publication Date:
20 January 2016 (online)

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Abstract

The first total synthesis of mirabiquinone A (2,3,5,6,8,10,11,13-octahydroxy-7-methyl-1H-dibenzo[b,h]xanthene-1,4,9,12(7H)-tetraone) produced by the sea urchin Scaphechinus mirabilis is described. This was achieved by cyclization of 6,6′-ethylidenebis(7-hydroxy-2,3-dimethoxynaphthazarin) or its mono- or dimethoxy derivatives and functional group deprotection. The synthesis of methyl analogues of mirabiquinone A is also described.

Key words

6,6′-ethylidenebis(2,3,7-trihydroxynaphthazarin) - cyclization - mirabiquinone A - dibenzo[b,h]xanthenetetraone - sea urchin Scaphechinus mirabilis

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560389.
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