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DOI: 10.1055/s-0032-1307549
Sterioselective Synthesis of S(-) Equol
Isoflavonoids are secondary metabolites of formonentin (1) and daidzein (2) obtained from plants and act as phytoalexins in the defense against pathogens of the plants[1]. When daidzein (2) is ingested into our body by eating soy and foods thereof, and is transformed to S(-) Equol (3) and other metabolites[2] by the intestinal micro flora such as gut microflora. S(-) Equol (3) which has a chiral center at the C3 position of the chroman ring stimulates the estrogenic response most effectively through binding to the Estrogenic Receptor β (ERβ)[3]. Enantiopure synthesis of S(-) Equol is essential to elucidate its detailed biological effects. In our group, a novel strategy for the enantioselective synthesis of S(-) Equol (3) using Evans alkylation as the critical chiral inducing reaction is presented and the full synthetic details will be presented.
Acknowledgements: The United States Department of Agriculture, Agricultural Research Service, Specific Cooperative Agreement No. 58–6408–2-0009 and the University of Illinois Botanical Research Center (BRC) entitled “Botanical Identification, Characterization, Quality Assurance and Quality Control“, funded by NIH, Prime award number 1P50AT006268–02. References: [1] Veitch NC (2007) Natural Product Reports 24: 417–464. [2] Chang Y-C, Nair MG (1995)J Nat Prod 58(12): 1892–1896. [3] Morito K, Hirose T, et al. (2001) Biological & Pharm Bull 24: 351–356.