{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,3]],"date-time":"2026-02-03T20:19:53Z","timestamp":1770149993256,"version":"3.49.0"},"reference-count":116,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2023,1,3]],"date-time":"2023-01-03T00:00:00Z","timestamp":1672704000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Natural Products and Medicinal Chemistry Research Group-CIIMAR","award":["UIDB\/04423\/2020"],"award-info":[{"award-number":["UIDB\/04423\/2020"]}]},{"name":"Natural Products and Medicinal Chemistry Research Group-CIIMAR","award":["UIDP\/04423\/2020"],"award-info":[{"award-number":["UIDP\/04423\/2020"]}]},{"name":"Natural Products and Medicinal Chemistry Research Group-CIIMAR","award":["PTDC\/CTA-AMB\/6686\/2020"],"award-info":[{"award-number":["PTDC\/CTA-AMB\/6686\/2020"]}]},{"name":"Natural Products and Medicinal Chemistry Research Group-CIIMAR","award":["PTDC\/CTAAMB\/0853\/2021"],"award-info":[{"award-number":["PTDC\/CTAAMB\/0853\/2021"]}]},{"name":"Natural Products and Medicinal Chemistry Research Group-CIIMAR","award":["Flav4Tumor-GI2-CESPU-2022"],"award-info":[{"award-number":["Flav4Tumor-GI2-CESPU-2022"]}]},{"name":"ERDF","award":["UIDB\/04423\/2020"],"award-info":[{"award-number":["UIDB\/04423\/2020"]}]},{"name":"ERDF","award":["UIDP\/04423\/2020"],"award-info":[{"award-number":["UIDP\/04423\/2020"]}]},{"name":"ERDF","award":["PTDC\/CTA-AMB\/6686\/2020"],"award-info":[{"award-number":["PTDC\/CTA-AMB\/6686\/2020"]}]},{"name":"ERDF","award":["PTDC\/CTAAMB\/0853\/2021"],"award-info":[{"award-number":["PTDC\/CTAAMB\/0853\/2021"]}]},{"name":"ERDF","award":["Flav4Tumor-GI2-CESPU-2022"],"award-info":[{"award-number":["Flav4Tumor-GI2-CESPU-2022"]}]},{"name":"CESPU","award":["UIDB\/04423\/2020"],"award-info":[{"award-number":["UIDB\/04423\/2020"]}]},{"name":"CESPU","award":["UIDP\/04423\/2020"],"award-info":[{"award-number":["UIDP\/04423\/2020"]}]},{"name":"CESPU","award":["PTDC\/CTA-AMB\/6686\/2020"],"award-info":[{"award-number":["PTDC\/CTA-AMB\/6686\/2020"]}]},{"name":"CESPU","award":["PTDC\/CTAAMB\/0853\/2021"],"award-info":[{"award-number":["PTDC\/CTAAMB\/0853\/2021"]}]},{"name":"CESPU","award":["Flav4Tumor-GI2-CESPU-2022"],"award-info":[{"award-number":["Flav4Tumor-GI2-CESPU-2022"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Stereoselective synthesis has been emerging as a resourceful tool because it enables the obtaining of compounds with biological interest and high enantiomeric purity. Flavonoids are natural products with several biological activities. Owing to their biological potential and aiming to achieve enantiomerically pure forms, several methodologies of stereoselective synthesis have been implemented. Those approaches encompass stereoselective chalcone epoxidation, Sharpless asymmetric dihydroxylation, Mitsunobu reaction, and the cycloaddition of 1,4-benzoquinone. Chiral auxiliaries, organo-, organometallic, and biocatalysis, as well as the chiral pool approach were also employed with the goal of obtaining chiral bioactive flavonoids with a high enantiomeric ratio. Additionally, the employment of the Diels\u2013Alder reaction based on the stereodivergent reaction on a racemic mixture strategy or using catalyst complexes to synthesise pure enantiomers of flavonoids was reported. Furthermore, biomimetic pathways displayed another approach as illustrated by the asymmetric coupling of 2-hydroxychalcones driven by visible light. Recently, an asymmetric transfer hydrogen-dynamic kinetic resolution was also applied to synthesise (R,R)-cis-alcohols which, in turn, would be used as building blocks for the stereoselective synthesis of flavonoids.<\/jats:p>","DOI":"10.3390\/molecules28010426","type":"journal-article","created":{"date-parts":[[2023,1,4]],"date-time":"2023-01-04T02:54:55Z","timestamp":1672800895000},"page":"426","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":28,"title":["Stereoselective Synthesis of Flavonoids: A Brief Overview"],"prefix":"10.3390","volume":"28","author":[{"given":"Ana Margarida","family":"Pereira","sequence":"first","affiliation":[{"name":"Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge de Viterbo Ferreira 228, 4050-313 Porto, Portugal"},{"name":"CIIMAR\u2014Interdisciplinary Centre of Marine and Environmental Research, University of Porto, Terminal de Cruzeiros do Porto de Leix\u00f5es, Avenida General Norton de Matos, s\/n, 4450-208 Matosinhos, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0715-1779","authenticated-orcid":false,"given":"Honorina","family":"Cidade","sequence":"additional","affiliation":[{"name":"Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge de Viterbo Ferreira 228, 4050-313 Porto, Portugal"},{"name":"CIIMAR\u2014Interdisciplinary Centre of Marine and Environmental Research, University of Porto, Terminal de Cruzeiros do Porto de Leix\u00f5es, Avenida General Norton de Matos, s\/n, 4450-208 Matosinhos, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3320-730X","authenticated-orcid":false,"given":"Maria Elizabeth","family":"Tiritan","sequence":"additional","affiliation":[{"name":"Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge de Viterbo Ferreira 228, 4050-313 Porto, Portugal"},{"name":"CIIMAR\u2014Interdisciplinary Centre of Marine and Environmental Research, University of Porto, Terminal de Cruzeiros do Porto de Leix\u00f5es, Avenida General Norton de Matos, s\/n, 4450-208 Matosinhos, Portugal"},{"name":"TOXRUN\u2014Toxicology Research Unit, University Institute of Health Sciences, CESPU, CRL, Rua Central de Gandra 1317, 4585-116 Gandra, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2023,1,3]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Dias, M.C., Pinto, D., and Silva, A.M.S. (2021). Plant flavonoids: Chemical characteristics and biological activity. Molecules, 26.","DOI":"10.3390\/molecules26175377"},{"key":"ref_2","first-page":"6792069","article-title":"Environmentally friendly methods for flavonoid extraction from plant material: Impact of their operating conditions on yield and antioxidant properties","volume":"2020","year":"2020","journal-title":"Sci. World J."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"3260","DOI":"10.1080\/14786419.2018.1470514","article-title":"Marine natural flavonoids: Chemistry and biological activities","volume":"33","author":"Martins","year":"2019","journal-title":"Nat. Prod. Res."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Liu, W., Feng, Y., Yu, S., Fan, Z., Li, X., Li, J., and Yin, H. (2021). The flavonoid biosynthesis network in plants. Int. J. Mol. Sci., 22.","DOI":"10.3390\/ijms222312824"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"978120","DOI":"10.3389\/fmed.2022.978120","article-title":"The potential of functionalized dressing releasing flavonoids facilitates scar-free healing","volume":"9","author":"Zhang","year":"2022","journal-title":"Front. Med."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2473","DOI":"10.1002\/ptr.6383","article-title":"Flavonoids as efficient scaffolds: Recent trends for malaria, leishmaniasis, Chagas disease, and dengue","volume":"33","author":"Boniface","year":"2019","journal-title":"Phytother. Res."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"113945","DOI":"10.1016\/j.biopha.2022.113945","article-title":"Anti-inflammatory and anti-allergic potential of dietary flavonoids: A review","volume":"156","author":"Rakha","year":"2022","journal-title":"Biomed. Pharmacother."},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Shamsudin, N.F., Ahmed, Q.U., Mahmood, S., Shah, S.A.A., Sarian, M.N., Khattak, M.M.A.K., Khatib, A., Sabere, A.S.M., Yusoff, Y.M., and Latip, J. (2022). Flavonoids as antidiabetic and anti-inflammatory agents: A review on structural activity relationship-based studies and meta-analysis. Int. J. Mol. Sci., 23.","DOI":"10.3390\/ijms232012605"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"3120","DOI":"10.1002\/ptr.7520","article-title":"Isobavachalcone: A comprehensive review of its plant sources, pharmacokinetics, toxicity, pharmacological activities and related molecular mechanisms","volume":"36","author":"Xing","year":"2022","journal-title":"Phytother. Res."},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Kashyap, P., Thakur, M., Singh, N., Shikha, D., Kumar, S., Baniwal, P., Yadav, Y.S., Sharma, M., Sridhar, K., and Inbaraj, B.S. (2022). In silico evaluation of natural flavonoids as a potential inhibitor of coronavirus disease. Molecules, 27.","DOI":"10.3390\/molecules27196374"},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Huang, W., Wang, Y., Tian, W., Cui, X., Tu, P., Li, J., Shi, S., and Liu, X. (2022). Biosynthesis investigations of terpenoid, alkaloid, and flavonoid antimicrobial agents derived from medicinal plants. Antibiotics, 11.","DOI":"10.3390\/antibiotics11101380"},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Dhaliwal, J.S., Moshawih, S., Goh, K.W., Loy, M.J., Hossain, M.S., Hermansyah, A., Kotra, V., Kifli, N., Goh, H.P., and Dhaliwal, S.K.S. (2022). Pharmacotherapeutics applications and chemistry of chalcone derivatives. Molecules, 27.","DOI":"10.3390\/molecules27207062"},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Luo, Y., Jian, Y., Liu, Y., Jiang, S., Muhammad, D., and Wang, W. (2022). Flavanols from nature: A phytochemistry and biological activity review. Molecules, 27.","DOI":"10.3390\/molecules27030719"},{"key":"ref_14","first-page":"5983","article-title":"Flavonoids: Molecular mechanism behind natural chemoprotective behavior-a mini review","volume":"12","author":"Gupta","year":"2022","journal-title":"Biointerface Res. Appl. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Pereira, D., Pinto, M., Correia-da-Silva, M., and Cidade, H. (2022). Recent advances in bioactive flavonoid hybrids linked by 1,2,3-triazole ring obtained by click chemistry. Molecules, 27.","DOI":"10.3390\/molecules27010230"},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Moreira, J., Almeida, J., Saraiva, L., Cidade, H., and Pinto, M. (2021). Chalcones as promising antitumor agents by targeting the p53 pathway: An overview and new insights in drug-likeness. Molecules, 26.","DOI":"10.3390\/molecules26123737"},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Khan, J., Deb, P.K., Priya, S., Medina, K.D., Devi, R., Walode, S.G., and Rudrapal, M. (2021). Dietary flavonoids: Cardioprotective potential with antioxidant effects and their pharmacokinetic, toxicological and therapeutic concerns. Molecules, 26.","DOI":"10.20944\/preprints202106.0305.v1"},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"Gervasi, T., Calderaro, A., Barreca, D., Tellone, E., Trombetta, D., Ficarra, S., Smeriglio, A., Mandalari, G., and Gattuso, G. (2022). Biotechnological applications and health-promoting properties of flavonols: An updated view. Int. J. Mol. Sci., 23.","DOI":"10.3390\/ijms23031710"},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Addi, M., Elbouzidi, A., Abid, M., Tungmunnithum, D., Elamrani, A., and Hano, C. (2022). An overview of bioactive flavonoids from citrus fruits. Appl. Sci., 12.","DOI":"10.3390\/app12010029"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"100694","DOI":"10.1016\/j.rineng.2022.100694","article-title":"Corrosion inhibitory potential of selected flavonoid derivatives: Electrochemical, molecular Zn surface interactions and quantum chemical approaches","volume":"16","author":"Sithuba","year":"2022","journal-title":"Results Eng."},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Singh Tuli, H. (2019). Chemistry and Synthetic Overview of Flavonoids. Current Aspects of Flavonoids: Their Role in Cancer Treatment, Springer.","DOI":"10.1007\/978-981-13-5874-6"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1852","DOI":"10.1039\/jr9530001852","article-title":"A new synthesis of isoflavones. Part I","volume":"381","author":"Baker","year":"1953","journal-title":"J. Chem. Soc. (Resumed)"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"A73","DOI":"10.1021\/ed072pA73.11","article-title":"The flavonoids: Advances in research since 1986","volume":"72","author":"Harborne","year":"1995","journal-title":"J. Chem. Educ."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"205","DOI":"10.1016\/S0031-9422(02)00116-4","article-title":"Genistein","volume":"60","author":"Dixon","year":"2002","journal-title":"Phytochemistry"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1542","DOI":"10.1016\/j.tetlet.2009.01.041","article-title":"A Wacker\u2013Cook synthesis of isoflavones: Formononetine","volume":"50","author":"Maldonado","year":"2009","journal-title":"Tetrahedron Lett."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1304","DOI":"10.1002\/hlca.201000400","article-title":"A novel synthesis of isoflavones via copper(I)-catalyzed intramolecular cyclization reaction","volume":"94","author":"Li","year":"2011","journal-title":"Helv. Chim. Acta"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"245","DOI":"10.1007\/s10600-005-0126-7","article-title":"Neoflavones. 2. Methods for synthesizing and modifying 4-arylcoumarins","volume":"41","author":"Garazd","year":"2005","journal-title":"Chem. Nat. Compd."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"2053","DOI":"10.1021\/jo202577m","article-title":"Palladium-catalyzed oxidative Heck coupling reaction for direct synthesis of 4-arylcoumarins using coumarins and arylboronic acids","volume":"77","author":"Li","year":"2012","journal-title":"J. Org. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Sharma, A., Sharma, P., Singh Tuli, H., and Sharma, A.K. (2018). Phytochemical and Pharmacological Properties of Flavonols. eLS, John Wiley & Sons, Inc.","DOI":"10.1002\/9780470015902.a0027666"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"502","DOI":"10.31788\/RJC.2019.1225020","article-title":"Efficient synthesis of chloro chalcones under ultrasound irradiation, their anticancer activities and molecular docking studies","volume":"12","author":"Suma","year":"2019","journal-title":"Rasayan J. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"654","DOI":"10.31788\/RJC.2020.1315534","article-title":"Synthesis of some chalcone derivatives, in vitro and in silico toxicity evaluation","volume":"13","author":"Kristanti","year":"2020","journal-title":"Rasayan J. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"9107","DOI":"10.1016\/j.tetlet.2003.10.060","article-title":"A new synthesis of flavonoids via Heck reaction","volume":"44","author":"Bianco","year":"2003","journal-title":"Tetrahedron Lett."},{"key":"ref_33","first-page":"e00394","article-title":"Sustainable Claisen-Schmidt chalcone synthesis catalysed by plasma-recovered MgO nanosheets from seawater","volume":"32","author":"Ekanayake","year":"2022","journal-title":"Sustain. Mater. Technol."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"182","DOI":"10.1246\/bcsj.10.182","article-title":"A new general method for the synthesis of the derivates of flavonol","volume":"10","author":"Taichiro","year":"1935","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1102","DOI":"10.1071\/CH14620","article-title":"Phase transfer catalysis extends the scope of the Algar\u2013Flynn\u2013Oyamada synthesis of 3-hydroxyflavones","volume":"68","author":"Nhu","year":"2015","journal-title":"Aust. J. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1780","DOI":"10.1139\/v90-277","article-title":"Stereoelectronic effects in ring closure reactions: The 2\u2032-hydroxychalcone\u2014Flavanone equilibrium, and related systems","volume":"68","author":"Brennan","year":"1990","journal-title":"Can. J. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"133","DOI":"10.1039\/b101826b","article-title":"Efficient conversion of 2\u2032-hydroxychalcones into flavanones and flavanols in a water suspension medium","volume":"3","author":"Tanaka","year":"2001","journal-title":"Green Chem."},{"key":"ref_38","doi-asserted-by":"crossref","unstructured":"Goud, B.S., Panneerselvam, K., Zacharias, D.E., and Desirajua, G.R. (1995). Intramolecular Michael-type addition in the solid state. J. Chem. Soc. Perkin Trans. 2, 325\u2013330.","DOI":"10.1039\/p29950000325"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"407","DOI":"10.1016\/S0040-4039(00)84031-9","article-title":"Electrochemical transformations of 2\u2032-hydroxychalcones into flavanoids","volume":"27","author":"Sanicanin","year":"1986","journal-title":"Tetrahedron Lett."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"3187","DOI":"10.1016\/S0040-4020(01)85950-0","article-title":"Photo-oxidative cyclisation of 2\u2032-hydroxychalcones leading to flavones induced by heterocycle n-oxides: High efficiency of pybimido[54-g]pteridine n-oxide for the photochemical dehydrogenation","volume":"44","author":"Maki","year":"1988","journal-title":"Tetrahedron"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"791","DOI":"10.1002\/jhet.123","article-title":"Ionic liquid catalyzed expeditious synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones and 2-aryl-2,3-dihydro-4H-chromen-4-ones under microwave irradiation","volume":"46","author":"Kumar","year":"2009","journal-title":"J. Heterocycl. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"220","DOI":"10.3184\/174751911X13014075196818","article-title":"An efficient catalytic synthesis of flavanones under green conditions","volume":"35","author":"Jiang","year":"2011","journal-title":"J. Chem. Res."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"14000","DOI":"10.1039\/D1RA01672E","article-title":"Divergent synthesis of flavones and flavanones from 2\u2032-hydroxydihydrochalcones via palladium(ii)-catalyzed oxidative cyclization","volume":"11","author":"Son","year":"2021","journal-title":"RSC Adv."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"3356","DOI":"10.1016\/j.bmc.2007.03.031","article-title":"Synthetic chalcones, flavanones, and flavones as antitumoral agents: Biological evaluation and structure\u2013activity relationships","volume":"15","author":"Cabrera","year":"2007","journal-title":"Bioorg. Med. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"909","DOI":"10.2298\/JSC120901119K","article-title":"Cyclization of 2\u2032-hydroxychalcones to flavones using ammonium iodide as an iodine source: An eco-friendly approach","volume":"78","author":"Kulkarni","year":"2013","journal-title":"J. Serb. Chem. Soc."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"13867","DOI":"10.1016\/S0040-4020(98)00853-9","article-title":"A short and facile synthetic route to prenylated flavones. Cyclodehydrogenation of prenylated 2\u2032-hydroxychalcones by a hypervalent iodine reagent","volume":"54","author":"Litkeia","year":"1998","journal-title":"Tetrahedron"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"225","DOI":"10.3184\/030823408X313591","article-title":"Sodium selenite-dimethylsulfoxide: A highly efficient reagent for dehydrogenation","volume":"2008","author":"Lamba","year":"2008","journal-title":"J. Chem. Res."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"253","DOI":"10.1016\/j.tetlet.2004.11.062","article-title":"Silica gel supported InBr3 and InCl3: New catalysts for the facile and rapid oxidation of 2\u2032-hydroxychalcones and flavanones to their corresponding flavones under solvent free conditions","volume":"46","author":"Ahmed","year":"2005","journal-title":"Tetrahedron Lett."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"6930","DOI":"10.1039\/c1ob06209c","article-title":"Ionic liquid mediated Cu-catalyzed cascade oxa-Michael-oxidation: Efficient synthesis of flavones under mild reaction conditions","volume":"9","author":"Du","year":"2011","journal-title":"Org. Biomol. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"2351","DOI":"10.1246\/bcsj.59.2351","article-title":"The direct preparation of flavones from 2\u2032-hydroxychalcones using disulfides","volume":"59","author":"Yukio","year":"1986","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1016\/j.cclet.2008.10.042","article-title":"Development of mild and efficient method for synthesis of substituted flavones using oxalic acid catalyst","volume":"20","author":"Zambare","year":"2009","journal-title":"Chin. Chem. Lett."},{"key":"ref_52","doi-asserted-by":"crossref","unstructured":"Wang, Z. (2010). Allan-Robinson Condensation. Comprehensive Organic Name Reactions, Wiley.","DOI":"10.1002\/9780470638859.conrr015"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1216","DOI":"10.1248\/cpb.37.1216","article-title":"Studies of the selective O-alkylation and dealkylation of flavonoids. XII.: A new, convenient method for synthesizing 3, 5-dihydroxy-6, 7-dimethoxyflavones from 3, 5, 6, 7-tetramethoxyflavones","volume":"37","author":"Horie","year":"1989","journal-title":"Chem. Pharm. Bull."},{"key":"ref_54","doi-asserted-by":"crossref","unstructured":"Li, J.J. (2009). Baker-Venkataraman rearrangement. Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications, Springer.","DOI":"10.1007\/978-3-642-01053-8_7"},{"key":"ref_55","doi-asserted-by":"crossref","unstructured":"Li, J.J. (2004). Other Six-Membered Heterocycles. Name Reactions in Heterocyclic Chemistry, John Wiley & Sons.","DOI":"10.1002\/0471704156"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"736","DOI":"10.1021\/jm00106a039","article-title":"4\u2032-Hydroxy-3-methoxyflavones with potent antipicornavirus activity","volume":"34","author":"DeMeyer","year":"1991","journal-title":"J. Med. Chem."},{"key":"ref_57","doi-asserted-by":"crossref","unstructured":"Wang, Z. (2010). Mentzer pyrone synthesis. Comprehensive Organic Name Reactions, Wiley.","DOI":"10.1002\/9780470638859"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"2855","DOI":"10.1021\/jo048685z","article-title":"Solvent-free synthesis of functionalized flavones under microwave irradiation","volume":"70","author":"Seijas","year":"2005","journal-title":"J. Org. Chem."},{"key":"ref_59","doi-asserted-by":"crossref","unstructured":"Pereira, D., Gon\u00e7alves, C., Martins, B.T., Palmeira, A., Vasconcelos, V., Pinto, M., Almeida, J.R., Correia-da-Silva, M., and Cidade, H. (2021). Flavonoid glycosides with a triazole moiety for marine antifouling applications: Synthesis and biological activity evaluation. Mar. Drugs, 19.","DOI":"10.3390\/md19010005"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"811","DOI":"10.1016\/j.tet.2017.12.052","article-title":"In memory of Prof. Venkataraman: Recent advances in the synthetic methodologies of flavones","volume":"74","author":"Kshatriya","year":"2018","journal-title":"Tetrahedron"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"5445291","DOI":"10.1155\/2022\/5445291","article-title":"Flavonoids a bioactive compound from medicinal plants and its therapeutic applications","volume":"2022","author":"Roy","year":"2022","journal-title":"Biomed Res. Int."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"4739","DOI":"10.3390\/molecules18044739","article-title":"Application of the Suzuki-Miyaura reaction in the synthesis of flavonoids","volume":"18","author":"Selepe","year":"2013","journal-title":"Molecules"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"3437","DOI":"10.1016\/S0040-4039(01)95429-2","article-title":"A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides","volume":"20","author":"Miyaura","year":"1979","journal-title":"Tetrahedron Lett."},{"key":"ref_64","doi-asserted-by":"crossref","unstructured":"Hurtov\u00e1, M., Biedermann, D., Osifov\u00e1, Z., Cva\u010dka, J., Valentov\u00e1, K., and K\u0159en, V. (2022). Preparation of synthetic and natural derivatives of flavonoids using Suzuki-Miyaura cross-coupling reaction. Molecules, 27.","DOI":"10.3390\/molecules27030967"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"114671","DOI":"10.1016\/j.ejmech.2022.114671","article-title":"What about the progress in the synthesis of flavonoid from 2020?","volume":"243","author":"Liu","year":"2022","journal-title":"Eur. J. Med. Chem."},{"key":"ref_66","doi-asserted-by":"crossref","unstructured":"Pinto, C., Cidade, H., Pinto, M., and Tiritan, M.E. (2021). Chiral flavonoids as antitumor agents. Pharmaceuticals, 14.","DOI":"10.3390\/ph14121267"},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"2145","DOI":"10.1016\/j.phytochem.2005.03.006","article-title":"Stereoselective synthesis of monomeric flavonoids","volume":"66","author":"Marais","year":"2005","journal-title":"Phytochemistry"},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"2236","DOI":"10.1021\/acs.jnatprod.6b00305","article-title":"Chiral separation of cytotoxic flavan derivatives from Daphne giraldii","volume":"79","author":"Li","year":"2016","journal-title":"J. Nat. Prod."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.ejmech.2017.03.072","article-title":"Autophagy antagonizes apoptosis induced by flavan enantiomers from Daphne giraldii in hepatic carcinoma cells in vitro","volume":"133","author":"Sun","year":"2017","journal-title":"Eur. J. Med. Chem."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.cbi.2018.04.014","article-title":"Flavan enantiomers from Daphne giraldii selectively induce apoptotic cell death in p53-null hepatocarcinoma cells in vitro","volume":"289","author":"Yao","year":"2018","journal-title":"Chem. Biol. Interact."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1016\/j.phytochem.2019.03.029","article-title":"Chiral separation, absolute configuration, and bioactivity of two pairs of flavonoid enantiomers from Morus nigra","volume":"163","author":"Xu","year":"2019","journal-title":"Phytochemistry"},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"7299","DOI":"10.1002\/chem.202001264","article-title":"Sterubin: Enantioresolution and configurational stability, enantiomeric purity in nature, and neuroprotective activity in vitro and in vivo","volume":"26","author":"Hofmann","year":"2020","journal-title":"Chem. Eur. J."},{"key":"ref_73","doi-asserted-by":"crossref","unstructured":"Grotewold, E. (2006). The Stereochemistry of Flavonoids. The Science of Flavonoids, Springer.","DOI":"10.1007\/978-0-387-28822-2"},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"1831","DOI":"10.1016\/S0040-4039(00)93796-1","article-title":"Catalytic asymmetric induction in oxidation reactions. The synthesis of optically active epoxides","volume":"17","author":"Helder","year":"1976","journal-title":"Tetrahedron Lett."},{"key":"ref_75","first-page":"1317","article-title":"Synthetic enzymes. Part 2. Catalytic asymmetric epoxidation by means of polyamino-acids in a triphase system","volume":"1","author":"Guixer","year":"1982","journal-title":"J. Chem. Soc. Perkin Trans."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"739","DOI":"10.1039\/a700550d","article-title":"Asymmetric epoxidation of enones employing polymeric \u03b1-amino acids in non-aqueous media","volume":"8","author":"Bentley","year":"1997","journal-title":"Chem. Commun."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"9727","DOI":"10.1016\/S0040-4020(99)00554-2","article-title":"Stereoselective synthesis of flavonoids. Part 7. Poly-oxygenated \u03b2-hydroxydihydrochalcone derivatives","volume":"55","author":"Nel","year":"1999","journal-title":"Tetrahedron"},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"7925","DOI":"10.1016\/S0040-4039(00)01382-4","article-title":"Enantioselective synthetic method for 3-hydroxyflavanones: An approach to (2R,3R)-3\u2032,4\u2032-O-dimethyltaxifolin","volume":"41","author":"Jew","year":"2000","journal-title":"Tetrahedron Lett."},{"key":"ref_79","first-page":"3415","article-title":"Enantioselective synthesis of flavonoids. Part 3.1trans- and cis-Flavan-3-ol methyl ether acetates","volume":"1997","author":"Ferreira","year":"1997","journal-title":"J. Chem. Soc. Perkin Trans. 1"},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"751","DOI":"10.1021\/acs.jafc.1c07229","article-title":"Condensed tannins, a viable solution to meet the need for sustainable and effective multifunctionality in food packaging: Structure, sources, and properties","volume":"70","author":"Panzella","year":"2022","journal-title":"J. Agric. Food Chem."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"8207","DOI":"10.1016\/j.tet.2004.06.113","article-title":"Enantioselective synthesis of afzelechin and epiafzelechin","volume":"60","author":"Wan","year":"2004","journal-title":"Tetrahedron"},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"2739","DOI":"10.1016\/S0040-4039(98)00299-8","article-title":"Asymmetric total synthesis of (+)-pisatin, a phytoalexin from garden peas (Pisum sativum L.)","volume":"39","author":"Pinard","year":"1998","journal-title":"Tetrahedron Lett."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"2391","DOI":"10.1021\/jo982164s","article-title":"Asymmetric reactions of 2-methoxy-1,4-benzoquinones with styrenyl systems:\u2009 enantioselective syntheses of 8-aryl-3-methoxybicyclo[4.2.0]oct-3-en-2,5-diones, 7-aryl-3-hydroxybicyclo[3.2.1]oct-3-en-2,8-diones, 2-aryl-6-methoxy-2,3-dihydrobenzofuran-5-ols, and pterocarpans","volume":"64","author":"Engler","year":"1999","journal-title":"J. Org. Chem."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"415","DOI":"10.1002\/jhet.4176","article-title":"Recent advances on the synthesis of flavans, isoflavans, and neoflavans","volume":"58","author":"Chinnabattigalla","year":"2021","journal-title":"J. Heterocycl. Chem."},{"key":"ref_85","doi-asserted-by":"crossref","unstructured":"Versteeg, M., Bezuidenhoudt, B.C.B., Ferreira, D., and Swart, K.J. (1995). The first enantioselective synthesis of isoflavonoids: (R)- and (S)-isoflavans. J. Chem. Soc. Chem. Commun., 1317\u20131318.","DOI":"10.1039\/c39950001317"},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"93","DOI":"10.1021\/acs.orglett.0c03766","article-title":"Asymmetric synthesis of ent-fissistigmatin C","volume":"23","author":"Xu","year":"2021","journal-title":"Org. Lett."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"8297","DOI":"10.1016\/S0040-4039(00)01464-7","article-title":"The first stereocontrolled synthesis of isoflavanones","volume":"41","author":"Vicario","year":"2000","journal-title":"Tetrahedron Lett."},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"3830","DOI":"10.1021\/ja070394v","article-title":"Catalytic enantioselective synthesis of flavanones and chromanones","volume":"129","author":"Biddle","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"7704","DOI":"10.1021\/jo101585t","article-title":"Organocatalyzed enantioselective protonation of silyl enol ethers: Scope, limitations and application to the preparation of enantioenriched homoisoflavones","volume":"75","author":"Poisson","year":"2010","journal-title":"J. Org. Chem."},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"820","DOI":"10.1039\/C7PY02050C","article-title":"Palladium-polymer nanoreactors for the aqueous asymmetric synthesis of therapeutic flavonoids","volume":"9","author":"Lestini","year":"2018","journal-title":"Polym. Chem."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"74","DOI":"10.1002\/chem.201203643","article-title":"Palladium-catalyzed asymmetric conjugate addition of arylboronic acids to heterocyclic acceptors","volume":"19","author":"Holder","year":"2013","journal-title":"Chemistry"},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"10082","DOI":"10.1021\/jacs.9b04472","article-title":"Total synthesis of caesalpinnone A and caesalpinflavan B: Evolution of a concise strategy","volume":"141","author":"Timmerman","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"1300","DOI":"10.1021\/ja412342g","article-title":"Simple, chemoselective hydrogenation with thermodynamic stereocontrol","volume":"136","author":"Iwasaki","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"3409","DOI":"10.1021\/acs.jafc.1c07557","article-title":"Asymmetric synthesis of sakuranetin-relevant flavanones for the identification of new chiral antifungal leads","volume":"70","author":"Yang","year":"2022","journal-title":"J. Agric. Food Chem."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"540","DOI":"10.1002\/asia.201403290","article-title":"Rhodium\/chiral diene-catalyzed asymmetric 1,4-addition of arylboronic acids to chromones: A highly enantioselective pathway for accessing chiral flavanones","volume":"10","author":"He","year":"2015","journal-title":"Chem. Asian J."},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"100627","DOI":"10.1016\/j.cogsc.2022.100627","article-title":"Chemoenzymatic synthesis of natural products using plant biocatalysts","volume":"35","author":"Nguyen","year":"2022","journal-title":"Curr. Opin. Green Sustain. Chem."},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"47","DOI":"10.1016\/j.molcatb.2014.08.006","article-title":"Enantioselective reduction of flavanone and oxidation of cis- and trans-flavan-4-ol by selected yeast cultures","volume":"109","author":"Janeczko","year":"2014","journal-title":"J. Mol. Catal. B Enzym."},{"key":"ref_98","doi-asserted-by":"crossref","first-page":"301","DOI":"10.1016\/j.jbiosc.2018.03.018","article-title":"Daidzein reductase of Eggerthella sp. YY7918, its octameric subunit structure containing FMN\/FAD\/4Fe-4S, and its enantioselective production of R-dihydroisoflavones","volume":"126","author":"Kawada","year":"2018","journal-title":"J. Biosci. Bioeng."},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"2000119","DOI":"10.1002\/biot.202000119","article-title":"Chemoenzymatic total syntheses of artonin I with an intermolecular Diels\u2013Alderase","volume":"15","author":"Liu","year":"2020","journal-title":"Biotechnol. J."},{"key":"ref_100","doi-asserted-by":"crossref","first-page":"111734","DOI":"10.1016\/j.mcat.2021.111734","article-title":"Stereoselective reduction of flavanones by marine-derived fungi","volume":"513","author":"Birolli","year":"2021","journal-title":"Mol. Catal."},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"10220","DOI":"10.1039\/D0SC04188B","article-title":"Design and synthesis of chiral and regenerable [2.2]paracyclophane-based NAD(P)H models and application in biomimetic reduction of flavonoids","volume":"11","author":"Zhu","year":"2020","journal-title":"Chem. Sci."},{"key":"ref_102","doi-asserted-by":"crossref","first-page":"1789","DOI":"10.1007\/s00044-014-1267-7","article-title":"Synthesis of novel amino acid derivatives containing chrysin as anti-tumor agents against human gastric carcinoma MGC-803 cells","volume":"24","author":"Song","year":"2015","journal-title":"Med. Chem. Res."},{"key":"ref_103","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1016\/j.jorganchem.2016.09.015","article-title":"Human topoisomerase I mediated cytotoxicity profile of l-valine-quercetin diorganotin(IV) antitumor drug entities","volume":"823","author":"Parveen","year":"2016","journal-title":"J. Organomet. Chem."},{"key":"ref_104","doi-asserted-by":"crossref","first-page":"4578","DOI":"10.1021\/acs.joc.7b00124","article-title":"Optimization of the synthesis of flavone\u2013amino acid and flavone\u2013dipeptide hybrids via Buchwald\u2013Hartwig reaction","volume":"82","author":"Varga","year":"2017","journal-title":"J. Org. Chem."},{"key":"ref_105","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1016\/j.omto.2020.08.018","article-title":"Antitumor activity in vivo and vitro of new chiral derivatives of baicalin and induced apoptosis via the PI3K\/Akt signaling pathway","volume":"19","author":"Hou","year":"2020","journal-title":"Mol. Ther. Oncolytics"},{"key":"ref_106","doi-asserted-by":"crossref","first-page":"13050","DOI":"10.1002\/chem.201602817","article-title":"The synthesis of trans-flavan-3-ol gallates by regioselective oxidative etherification and their cytotoxicity mediated by 67\u2009LR","volume":"22","author":"Shiraishi","year":"2016","journal-title":"Chemistry"},{"key":"ref_107","doi-asserted-by":"crossref","first-page":"9257","DOI":"10.1002\/anie.201404499","article-title":"Enantioselective biomimetic total syntheses of kuwanons\u2005I and J and brosimones\u2005A and B","volume":"53","author":"Han","year":"2014","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_108","doi-asserted-by":"crossref","first-page":"458","DOI":"10.1021\/acs.joc.5b02248","article-title":"Chiral boron complex-promoted asymmetric Diels\u2013Alder cycloaddition and its application in natural product synthesis","volume":"81","author":"Li","year":"2016","journal-title":"J. Org. Chem."},{"key":"ref_109","doi-asserted-by":"crossref","first-page":"798","DOI":"10.1021\/jacs.5b12778","article-title":"Asymmetric syntheses of the flavonoid Diels-Alder natural products sanggenons C and O","volume":"138","author":"Qi","year":"2016","journal-title":"J. Am. Chem. Soc."},{"key":"ref_110","doi-asserted-by":"crossref","first-page":"29005","DOI":"10.1039\/C9RA07198A","article-title":"A bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light","volume":"9","author":"Gao","year":"2019","journal-title":"RSC Adv."},{"key":"ref_111","doi-asserted-by":"crossref","first-page":"9775","DOI":"10.1021\/jacs.6b05939","article-title":"Biomimetic approach to the catalytic enantioselective synthesis of flavonoids","volume":"138","author":"Yang","year":"2016","journal-title":"J. Am. Chem. Soc."},{"key":"ref_112","doi-asserted-by":"crossref","first-page":"2981","DOI":"10.1021\/acs.orglett.7b01218","article-title":"Enantioselective synthesis of isoflavanones by catalytic dynamic kinetic resolution","volume":"19","author":"Qin","year":"2017","journal-title":"Org. Lett."},{"key":"ref_113","doi-asserted-by":"crossref","first-page":"3091","DOI":"10.1038\/s41467-020-16933-y","article-title":"Asymmetric one-pot transformation of isoflavones to pterocarpans and its application in phytoalexin synthesis","volume":"11","author":"Ciesielski","year":"2020","journal-title":"Nat. Commun."},{"key":"ref_114","doi-asserted-by":"crossref","first-page":"4849","DOI":"10.1021\/acs.joc.0c02981","article-title":"Asymmetric transfer hydrogenation of arylidene-substituted chromanones and tetralones catalyzed by Noyori\u2013Ikariya Ru(II) complexes: One-pot reduction of C=C and C=O bonds","volume":"86","author":"Caleffi","year":"2021","journal-title":"J. Org. Chem."},{"key":"ref_115","doi-asserted-by":"crossref","first-page":"5097","DOI":"10.1002\/cctc.202101252","article-title":"Enantioselective synthesis of isoflavanones and pterocarpans through a RuII-catalyzed ATH-DKR of isoflavones","volume":"13","author":"Gaspar","year":"2021","journal-title":"ChemCatChem"},{"key":"ref_116","doi-asserted-by":"crossref","first-page":"1156","DOI":"10.1039\/C8NP00069G","article-title":"Isolation of naturally occurring novel isoflavonoids: An update","volume":"36","year":"2019","journal-title":"Nat. Prod. Rep."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/1\/426\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T17:57:21Z","timestamp":1760119041000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/1\/426"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,1,3]]},"references-count":116,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2023,1]]}},"alternative-id":["molecules28010426"],"URL":"https:\/\/doi.org\/10.3390\/molecules28010426","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,1,3]]}}}