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Total Synthesis of Licochalcone E

  • Yoon, Goo (College of Pharmacy and Research Institute of Drug Development, Chonnam National University) ;
  • Liu, Zhiguo (Korea Institute of Science and Technology, Gangneung Institute) ;
  • Jeong, Hee-Jin (College of Pharmacy and Research Institute of Drug Development, Chonnam National University) ;
  • Cheon, Seung-Hoon (College of Pharmacy and Research Institute of Drug Development, Chonnam National University)
  • Published : 2009.12.20

Abstract

Total synthesis of (${\pm}$)-licochalcone E (1), an allyl retrochalcone isolated from roots of Glycyrrhiza inflata, has been achieved from 4-tetrahydropyranyloxyacetophenone (7) with (E)-2-methoxy-4-(2-methyl-2-butenyloxy)benzaldehyde (6) or (Z)-2-methoxy-4-(2-methyl-2-butenyloxy)-benzaldehyde (11) through a convergent strategy involving aldol condensation and Claisen rearrangement as key steps.

Keywords

References

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  2. ChemInform Abstract: Total Synthesis of Licochalcone E (V) vol.41, pp.18, 2010, https://doi.org/10.1002/chin.201018212
  3. Semisynthesis of Licochalcone E and Biological Evaluation as Vasorelaxant Agents vol.31, pp.4, 2009, https://doi.org/10.5012/bkcs.2010.31.04.1085
  4. A Journey Towards Natural Licochalcone E: From Isolation to Asymmetric Total Synthesis vol.34, pp.8, 2009, https://doi.org/10.1007/s12272-011-0800-1
  5. Highly Efficient Synthesis of Licochalcone E through Water-Accelerated [3,3]-Sigmatropic Rearrangement of Allyl Aryl Ether vol.32, pp.3, 2009, https://doi.org/10.5012/bkcs.2011.32.3.1059
  6. Synthetic methods and biological applications of retrochalcones isolated from the root of Glycyrrhiza species: A review vol.3, pp.None, 2009, https://doi.org/10.1016/j.rechem.2021.100216