Studies on the oxidative cyclization of 3-hydroxyalkyl-1,2,4-trialkoxynaphthalenes and synthetic application for the biologically active natural compound rhinacanthone |
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Authors: | Tokutaro Ogata Misae Doe Aya Matsubara Eri Torii Chiaki Nishiura Arisa Nishiuchi Yusuke Kobayashi Tetsutaro Kimachi |
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Institution: | 1. School of Pharmaceutical Sciences, Mukogawa Women''s University, 11-68 Koshien Kyu-bancho, Nishinomiya 663-8179, Hyogo, Japan;2. Graduate School and Faculty of Pharmaceutical Sciences, Kyoto University, 46-29 Yoshida Shimoadachicho, Sakyo-ku, Kyoto 606-8501, Japan |
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Abstract: | The oxidative intramolecular cyclization of 3-hydroxyalkyl-1,2,4-trimethoxynaphthalenes was investigated. A series of 1,2-naphthoquinone fused cyclic ethers were synthesized directly from 3-hydroxyalkyl-1,2,4-trimethoxynaphthalenes by exposure to diammonium cerium (IV) nitrate. To understand the reaction mechanism, the intramolecular cyclization of 3-hydroxyalkyl-naphthoquinones that were formed as reaction intermediates was also examined. The results suggested that the reaction proceeds by a stepwise oxidation–cyclization mechanism. Using this methodology, five-step synthesis of rhinacanthone was achieved with high yield. |
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Keywords: | Oxidative cyclization Diammonium cerium (IV) nitrate Naphthoquinone Natural product |
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