A convenient synthesis of naturally occurring quinizarins |
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| Affiliation: | 1. College of Science, Northwest A&F University, 22 Xinong Road, Shaanxi, Yangling, 712100, China;2. Department of Natural Products Chemistry, School of Pharmacy Fudan University, 826 Zhangheng Road, Shanghai 201203, China;1. Instituto Federal de Minas Gerais (IFMG), Campus Ouro Branco, CEP 36420-000, Ouro Branco, MG, Brazil;2. Chemistry Department, Universidade Federal de Viçosa, CEP 36570-900, Viçosa, MG, Brazil;3. Chemistry Department, Universidade Federal de Minas Gerais, CEP 3409-5720, Belo Horizonte, MG, Brazil;4. Inorganic Chemistry Department, Universidade Federal Fluminense, CEP 24020-141, Niterói, RJ, Brazil;5. Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK |
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| Abstract: | A general and regiospecific method for the preparation of quinizarins involves the cycloaddition of electron-rich dienes. Advantageous syntheses of several natural products, 2-methylquinizarin, islandicin, digitopurpone, erythroglaucin, 5-0-methylislandicin and 8-0-methyl-digitopurpone illustrate this procedure. A structure attributed to ventinone B is incorrect and 1,4,8-trihydroxy-6-methylanthraquinone is different from a natural substance so described. |
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