Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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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)
  • Received : 2010.11.05
  • Accepted : 2010.12.07
  • Published : 2011.02.20
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Abstract

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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References

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