Abstract
The synthesis of (+)-licochalcone E (1) was accomplished for the first time in 13 steps from aryl bromide (6) with 8% overall yield. Palladium-catalyzed Negishi-Reformatsky coupling reaction of compound 6 with ethyl 2-(tributylstannyl)acetate provided the aryl acetic ester (5), which was converted to aryl acetamide (4) via mixed anhydride formation. Chiral auxiliarymediated methylation of the (S)-4-benzyl-2-oxazolidinone-derived aryl acetamide (4) provided the key asymmetric benzylic methyl group in compound 1.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Chang, H. J., Yoon, G., Park, J. S., Kim, M. H., Baek, M. K., Kim, N. H., Shin, B. A., Ahn, B. W., Cheon, S. H., and Jung, Y. D., Induction of apoptosis by the licochalcone E in endothelial cells via modulation of NF-kappaB and Bcl-2 Family. Biol. Pharm. Bull., 30, 2290–2293 (2007).
Ghosh, A. K. and Gong, G., Total synthesis and structural revision of (+)-amphidinolide W. J. Am. Chem. Soc., 126, 3704–3705 (2004).
Heckrodt, T. J. and Mulzer, J., Total synthesis of Elisabethin A: intramolecular Diels-Alder reaction under biomimetic conditions. J. Am. Chem. Soc., 125, 4680–4681 (2003).
Kosugi, M., Negishi, Y., Kameyama, M., and Migita, T., Palladium-catalyzed displacement of aryl halide by the tin analogue of Reformatsky reagent. Bull. Chem. Soc. Jpn., 58, 3383–3384 (1985).
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).
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).
Nomura, T. and Fukai, T., Phenolic constituents of licorice (Glycyrrhiza species). Fortschr. Chem. Org. Naturst., 73, 1–158 (1998).
Qin, Y. C., Stivala, C. E., and Zakarian, A., Acyclic stereocontrol in the Ireland-Claisen rearrangement of alpha-branched esters. Angew. Chem. Int. Ed. Engl., 46, 7466–7469 (2007).
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., Kang, B. Y., and Cheon, S. H., Topoisomerase I inhibition and cytotoxicity of licochalcones A and E from Glycyrrhiza inflata. Arch. Pharm. Res., 30, 313–316 (2007).
Yoon, G., Lee, W., Kim, S. N., and Cheon, S. H., Inhibitory effect of chalcones and their derivatives from Glycyrrhiza inflata on protein tyrosine phosphatase 1B. Bioorg. Med. Chem. Lett., 19, 5155–5157 (2009a).
Yoon, G., Liu, Z., Jung, H. J., and Cheon, S. H., Total synthesis of licochalcone E. Bull. Korean Chem. Soc., 30, 2959–2961 (2009b).
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).
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Liu, Z., Wang, Z., Yoon, G. et al. Stereoselective total synthesis of (+)-licochalcone E. Arch. Pharm. Res. 34, 1269–1276 (2011). https://doi.org/10.1007/s12272-011-0805-9
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-011-0805-9