Abstract
Due to the promising biological activities of licochalcone E first isolated from Glycyrrhiza inflate, several synthetic efforts have been made to obtain this valuable natural product in a large scale. In this issue, Cheon et al. (Liu et al., 2011) accomplished the stereoselective synthesis of (R)-(+)-licochalcone E. This report covers licochalcone E from isolation to the stereoselective total synthesis.
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Cho, Y. C., Lee, S. H., Yoon, G., Kim, H. S., Na, J. Y., Choi, H. J., Cho, C. W., Cheon, S. H., and Kang, B. Y., Licochalcone E reduces chronic allergic contact dermatitis and inhibits IL-12p40 production through down-regulation of NF-κB. Int. Immunopharmacol., 10, 1119–1126 (2010).
Jeon, J. H., Kim, M. R., Kwon, E. M., Lee, N. R., and Jun, J. G., Highly efficient synthesis of licochalcone E through water-accelerated [3,3]-sigmatropic rearrangement of allyl aryl ether. Bull. Korean Chem. Soc., 32, 1059–1062 (2011).
Kajiyama, K., Demizu, S., Hiraga, Y., Kinoshita, K., Koyama, K., Takahashi, K., Tamura, Y., Okada, K., and Kinoshita, T., Two prenylated retrochalcones from Glycyrrhiza inflata. Phytochemistry, 31, 3229–3232 (1992).
Li, J., Mi, Y., He, J., and Deng, X., A short and efficient synthesis of licochalcone E. Synlett, 2289–2292 (2010).
Liu, Z., Yoon, G., and Cheon, S. H., An enantioselective total synthesis of (S)-(-)-licochalcone E: determination of the absolute configuration. Tetrahedron, 66, 3165–3172 (2010).
Liu, Z., Wang, Z., Yoon, G., and Cheon, S. H., Stereoselective total synthesis of (+)-licochalcone E. Arch. Pharm. Res., 34, 1269–1276 (2011).
Na, Y., Cha, J.-H., Yoon, H. G., and Kwon, Y., A concise synthesis of licochalcone E and its regio-isomer, licochalcone F. Chem. Pharm. Bull., 57, 607–609 (2009).
Saitoh, T. and Shibata, S., New type chalcones from licorice root. Tetrahedron Lett., 16, 4461–4462 (1975).
Schobert, R., Siegfried, S., Gordon, G., Mulholland, D., and Nieuwenhuyzen, M., Abnormal Claisen rearrangements of tetronates and stereoselective ring opening of intermediate spirocyclopropanes. Tetrahedron Lett., 42, 4561–4564 (2001).
Yoon, G., Jung, Y. D., and Cheon, S. H., Cytotoxic allyl retrochalcone from the roots of Glycyrrhiza inflata. Chem. Pharm. Bull., 53, 694–695 (2005).
Yoon, G., Liu, Z., Jeong, H. J., and Cheon, S. H., Total synthesis of licochalcone E. Bull. Korean Chem. Soc., 30, 2959–2961 (2009).
Yoon, G., Oak, M. H., Lee, J. O., and Cheon, S. H., Semisynthesis of licochalcone E and biological evaluation as vasorelaxant agents. Bull. Korean Chem. Soc., 31, 1085–1087 (2010).
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Ryu, JS. A journey towards natural licochalcone E: From isolation to asymmetric total synthesis. Arch. Pharm. Res. 34, 1219–1222 (2011). https://doi.org/10.1007/s12272-011-0800-1
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DOI: https://doi.org/10.1007/s12272-011-0800-1