Bulletin of the Korean Chemical Society

  • 제32권1호
  • /
  • Pages.153-156
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  • 2011
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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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)
  • 투고 : 2010.09.29
  • 심사 : 2010.11.05
  • 발행 : 2011.01.20
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초록

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.

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피인용 문헌

  1. ChemInform Abstract: Concise Synthesis of (.+-.)-Rhinacanthin A (VI), Dehydro α-Lapachone (IV), and β-Lapachone (VIII), and Pyranonaphthoquinone Derivatives (XII). vol.42, pp.23, 2011, https://doi.org/10.1002/chin.201123199
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  4. Construction of Cyclic Ether-Fused Tricyclic Naphthoquinone Derivatives by Intramolecular Cyclization Reaction vol.97, pp.1, 2018, https://doi.org/10.3987/REV-18-SR(T)2
  5. UV–VIS spectral and GC–MS characterization of Handroanthus serratifolius (Vahl.) Grose (a.k.a. Tabebuia serratifolia (Vahl.) Nichols/Lapacho) heartwood main extractives: a comparison of protocols aimed at a practical evaluation of Lapachol and Dehydro-α-Lapachone content vol.76, pp.5, 2018, https://doi.org/10.1007/s00107-018-1331-y