Synthesis of lomazarin and norlomazarin, pigments from Lomandra hastilis |
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| Authors: | D. N. Pelageev M. N. Panchenko N. D. Pokhilo V. A. Denisenko V. F. Anufriev |
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| Affiliation: | (1) Pacific Institute of Bioorganic Chemistry, Far-East Branch, Russian Academy of Sciences, Russian Federation, 690022, Vladivostok, prosp, 100-Letiya Vladivostoka, 159, Russia;(2) Institute of Chemistry and Applied Ecology, Far-East State University, Russian Federation, 690600, Vladivostok, ul. Oktyabr’skaya, 27, Russia |
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| Abstract: | 5,8-Dihydroxy-2,3,6-trimethoxy-7-ethyl-1,4-naphthoquinone (1) was used to synthesize in high yield 5,8-dihydroxy-7(1′-hydroxyethyl)-2,3,6-trimethoxy-1,4-naphthoquinone (lomazarin, 3), a pigment from Lomandra hastilis. Alkaline hydrolysis of lomazarin produced mainly 5,6,8-trihydroxy-2,3-dimethoxy-1,4-naphthoquinone (9) through a retro-aldol decomposition of the 6-keto-form of 5,6,8-trihydroxy-7(1′-hydroxyethyl)-2,3-dimethoxy-1,4-naphthoquinone (13b) formed during the reaction. 2,5,8-Trihydroxy-7(1′-hydroxyethyl)-3,6-dimethoxy-1,4-naphthoquinone (norlomazarin, 4a), a pigment of L. hastilis, and its 3,5,8-trihydroxy-7(1′-hydroxyethyl)-2,6-dimethoxy isomer 4b were formed as a difficultly separable mixture in addition to quinone 9. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 581–584, November–December, 2008. |
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| Keywords: | echinochrome trimethyl ether lomazarin norlomazarin Lomandra hastilis retro-aldol reaction spinochrome D dimethyl ether Echinotrix calamaris tricrozarin B Tritonia crocosmaeflora |
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