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http://dx.doi.org/10.5012/bkcs.2011.32.1.153

Concise Synthesis of (±)-Rhinacanthin A, Dehydro α-Lapachone, and β-Lapachone, and Pyranonaphthoquinone Derivatives  

Wang, Xue (School of Chemical Engineering and Technology, Yeungnam University)
Chen, Ye (School of Chemical Engineering and Technology, Yeungnam University)
Lee, Yong-Rok (School of Chemical Engineering and Technology, Yeungnam University)
Publication Information
Bulletin of the Korean Chemical Society / v.32, no.1, 2011 , pp. 153-156 More about this Journal
Abstract
A concise synthesis of (${\pm}$)-rhinacanthin A is achieved in two steps by epoxidation of dehydro-$\alpha$-lapachone, followed by chemo- and regioselective reduction. Dehydro-$\alpha$-lapachone was also synthesized in two steps starting from 4-methoxy-1-naphthol by ethylenediamine diaetate (EDDA)-catalyzed benzopyran formation and a CAN-mediated oxidation reaction. $\beta$-Lapachone was synthesized in three steps from 4-methoxy-1-naphthol by benzopyran formation, catalytic hydrogenation, and Jones oxidation. As additional reactions, synthesis of pyranonaphthoquinone derivatives with the pyranokunthone B skeleton has been achieved in a single step from readily available 2-hydroxy-6-methoxy-1,4-naphthoquinone and 2-hydroxy-7-methoxy-1,4-naphthoquinone.
Keywords
Pyranonaphthoquinones; Rhinacanthin A; Dehydro-$\alpha$-lapachone; $\beta$-Lapachone;
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