Bulletin of the Korean Chemical Society

  • 제32권2호
  • /
  • Pages.566-570
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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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Efficient Synthesis of Bibenzyl Derivatives Bearing Pyranyl Moieties: First Total Synthesis of Bauhinol D

  • Park, Byung-Ho (School of Chemical Engineering and Technology, Yeungnam University) ;
  • Lee, Yong-Rok (School of Chemical Engineering and Technology, Yeungnam University) ;
  • Kim, Sung-Hong (Analysis Research Division, Daegu Center, Korea Basic Science Institute)
  • 투고 : 2010.11.05
  • 심사 : 2010.12.07
  • 발행 : 2011.02.20
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초록

An efficient and general synthesis of bibenzyl derivatives bearing pyranyl rings was achieved by ethylenediamine diacetate-catalyzed reactions of 3,5-dihydroxybibenzyl with ${\alpha},{\beta}$-unsaturated aldehydes in moderate yields. These reactions provided naturally occurring compounds 1 and 2 in single step reaction. As an application of this methodology, biologically interesting natural bauhinol D (8) was synthesized by a convergent sequence from readily available benzaldehyde and benzyl phosphonate.

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피인용 문헌

  1. ChemInform Abstract: Efficient Synthesis of Bibenzyl Derivatives Bearing Pyranyl Moieties: First Total Synthesis of Bauhinol D. vol.42, pp.28, 2011, https://doi.org/10.1002/chin.201128199
  2. Homo- and Hetero-oxidative Coupling of Benzyl Anions vol.77, pp.6, 2012, https://doi.org/10.1021/jo3000805
  3. A Common Building Block for the Syntheses of Amorfrutin and Cajaninstilbene Acid Libraries toward Efficient Binding with Peroxisome Proliferator-Activated Receptors vol.17, pp.2, 2015, https://doi.org/10.1021/ol503135u