Synthesis of Mansonone F Based on the Regioselective Hydrolysis of a Hydroquinone Diacetate
The synthesis of mansonone F (1), an antimicrobial sesquiterpenequinone, is described. Starting from 2,5-dimethyl-1,4-naphthoquinone (5), the corresponding selectively protected hydroquinone 9 was prepared in four steps. Alkylation of 9 using chloroacetone, cyclization, and oxidation to the o-quinon...
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Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 1999-12, Vol.62 (12), p.1643-1645 |
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Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | The synthesis of mansonone F (1), an antimicrobial sesquiterpenequinone, is described. Starting from 2,5-dimethyl-1,4-naphthoquinone (5), the corresponding selectively protected hydroquinone 9 was prepared in four steps. Alkylation of 9 using chloroacetone, cyclization, and oxidation to the o-quinone completed the reaction sequence in 7.5% overall yield. The regioselectivity for the basic hydrolysis of hydroquinone diacetate 6 was discussed on the basis of MO calculations. |
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ISSN: | 0163-3864 1520-6025 |
DOI: | 10.1021/np990277g |