Heo, MyunghoeLee, BitSishtla, KamakshiFei, XiangLee, SanhaPark, SoojunYuan, YueLee, SeulKwon, SangilLee, JungeunKim, SangheeCorson, Timothy W.Seo, Seung-Yong2021-04-132021-04-132019-08-05Heo, M., Lee, B., Sishtla, K., Fei, X., Lee, S., Park, S., Yuan, Y., Lee, S., Kwon, S., Lee, J., Kim, S., Corson, T. W., & Seo, S.-Y. (2019). Enantioselective Synthesis of Homoisoflavanones by Asymmetric Transfer Hydrogenation and Their Biological Evaluation for Antiangiogenic Activity. The Journal of Organic Chemistry, 84(16), 9995–10011. https://doi.org/10.1021/acs.joc.9b011340022-3263https://hdl.handle.net/1805/25627Neovascular eye diseases are a major cause of blindness. Excessive angiogenesis is a feature of several conditions, including wet age-related macular degeneration, proliferative diabetic retinopathy, and retinopathy of prematurity. Development of novel anti-angiogenic small molecules for the treatment of neovascular eye disease is essential to provide new therapeutic leads for these diseases. We have previously reported the therapeutic potential of anti-angiogenic homoisoflavanone derivatives with efficacy in retinal and choroidal neovascularization models, although these are racemic compounds due to the C3-stereogenic center in the molecules. This work presents asymmetric synthesis and structural determination of anti-angiogenic homoisoflavanones and pharmacological characterization of the stereoisomers. We describe an enantioselective synthesis of homoisoflavanones by virtue of ruthenium-catalyzed asymmetric transfer hydrogenation accompanying dynamic kinetic resolution, providing a basis for the further development of these compounds into novel experimental therapeutics for neovascular eye diseases.en-USHomoisoflavanone3-Benzyl-chroman-4-one3-Benzyl-chroman-4-olAsymmetric transfer hydrogenationDynamic kinetic resolutionAngiogenesisOcular neovascularizationArticle