A practical total synthesis of wedelolactone

References

• Govindachari, T. R.; Nagarajan, K.; Pai, B. R. Chemical Examination of Wedelia calendulacea. Part I. structure of Wedelolactone. J. Chem. Soc. 1956, 126, 629–632. DOI: 10.1039/jr9560000629.
   Google Scholar
• Ha, N. M.; Hop, N. Q.; Son, N. T. Wedelolactone: A Molecule of Interests. Fitoterapia 2023, 164, 105355. DOI: 10.1016/j.fftote.2022.105355.
   PubMed Web of Science ®Google Scholar
• Lu, Y.; Hu, D.; Ma, S.; Zhao, X.; Wang, S.; Wei, G.; Wang, X.; Wen, A.; Wang, J. Protective Effect of Wedelolactone against CCl4-Induced Acute Liver Injury in Mice. Int. Immunopharmacol. 2016, 34, 44–52. DOI: 10.1016/j.intimp.2016.02.003.
   PubMed Web of Science ®Google Scholar
• Huston, W. M.; Gloeckl, S.; de Boer, L.; Beagley, K. W.; Timms, P. Apoptosis is Induced in Chlamydia trachomatis-Infected HEp-2 Cells by the Addition of a Combination Innate Immune Activation Compounds and the Inhibitor Wedelolactone. Am. J. Reprod. Immunol. 2011, 65, 460–465. DOI: 10.1111/j.1600-0897.2010.00936.x.
   PubMed Web of Science ®Google Scholar
• Sarveswaran, S.; Ghosh, R.; Parikh, R.; Ghosh, J. Wedelolactone, an Anti-Inflammatory Botanical, Interrupts c-Myc Oncogenic Signaling and Synergizes with Enzalutamide to Induce Apoptosis in Prostate Cancer Cells. Mol. Cancer Ther. 2016, 15, 2791–2801. DOI: 10.1158/1535-7163.MCT-15-0861.
   PubMed Web of Science ®Google Scholar
• Deng, X.; Liang, L.-N.; Zhu, D.; Zheng, L.-P.; Yu, J.-H.; Meng, X.-L.; Zhao, Y.-N.; Sun, X.-X.; Pan, T.-W.; Liu, Y.-Q. Wedelolactone Inhibits Osteoclastogenesis but Enhances Osteoblastogenesis through Altering Different Semaphorins Production. Int. Immunopharmacol. 2018, 60, 41–49. DOI: 10.1016/j.intimp.2018.04.037.
   PubMed Web of Science ®Google Scholar
• Xia, Y.; Chen, J.; Cao, Y.; Xu, C.; Li, R.; Pan, Y.; Chen, X. Wedelolactone Exhibits anti-Fibrotic Effects on Human Hepatic Stellate Cell Line LX-2. Eur. J. Pharmacol. 2013, 714, 105–111. DOI: 10.1016/j.ejphar.2013.06.012.
   PubMed Web of Science ®Google Scholar
• Zhang, X.; Li, N.; Liu, Y.; Ji, B.; Wang, Q.; Wang, M.; Dai, K.; Gao, D. On-Demand Drug Release of ICG-Liposomal Wedelolactone Combined Photothermal Therapy for Tumor. Nanomedicine 2016, 12, 2019–2029. DOI: 10.1016/j.nano.2016.05.013.
   PubMed Web of Science ®Google Scholar
• Das, S.; Mukherjee, P.; Chatterjee, R.; Jamal, Z.; Chatterji, U. Enhancing Chemosensitivity of Breast Cancer Stem Cells by Downregulating SOX2 and ABCG2 Using Wedelolactone-Encapsulated NanoparticlesDrug Nanoformulation Enhances Chemosensitivity of Breast CSC. Mol. Cancer Ther. 2019, 18, 680–692. DOI: 10.1158/1535-7163.MCT-18-0409.
   PubMed Web of Science ®Google Scholar
• Nehybová, T.; Šmarda, J.; Daniel, L.; Stiborek, M.; Kanický, V.; Spasojevič, I.; Preisler, J.; Damborský, J.; Beneš, P. Wedelolactone Acts as Proteasome Inhibitor in Breast Cancer Cells. IJMS 2017, 18, 729. DOI: 10.3390/ijms18040729.
   Google Scholar
• Achari, A.; Chatterjee, S.; Dey, S.; Kundu, T. K.; Jaisankar, P. Catecholase-Catalyzed Synthesis of Wedelolactone, a Natural Coumestan and Its Analogs. Org. Biomol. Chem. 2022, 21, 89–92. DOI: 10.1039/d2ob02081e.
   PubMed Web of Science ®Google Scholar
• Li, C. C.; Xie, Z. X.; Zhang, Y. D.; Chen, J. H.; Yang, Z. Total Synthesis of Wedelolactone. J. Org. Chem. 2003, 68, 8500–8504. DOI: 10.1021/jo030228f.
   PubMedGoogle Scholar
• Chang, C.; Yang, L.; Chang, S.; Fang, Y.; Lee, Y. Total Synthesis of Demethylwedelolactone and Wedelolactone by Cu-Mediated/Pd(0)-Catalysis and Oxidative-Cyclization. Tetrahedron 2008, 64, 3661–3666. DOI: 10.1016/j.tet.2008.02.031.
   Web of Science ®Google Scholar
• Kelly, T. R.; Szabados, A.; Lee, Y. J. Total Synthesis of Garcifuran B. J. Org. Chem. 1997, 62, 428–429. DOI: 10.1021/jo9615662.
   PubMedGoogle Scholar
• Huang, H. D.; Chen, J. Q.; Ren, J.; Zhang, C. F.; Ji, F. Palladium(II)-Catalyzed Efficient Synthesis of Wedelolactone and Evaluation as Potential Tyrosinase Inhibitor. Molecules 2019, 24, 4130. DOI: 10.3390/molecules24224130.
   PubMed Web of Science ®Google Scholar
• Hofmann, J.; Fayez, S.; Scheiner, M.; Hoffmann, M.; Oerter, S.; Appelt-Menzel, A.; Maher, P.; Maurice, T.; Bringmann, G.; Decker, M. Sterubin: Enantioresolution and Configurational Stability, Enantiomeric Purity in Nature, and Neuroprotective Activity In Vitro and In Vivo. Chemistry 2020, 26, 7299–7308. DOI: 10.1002/chem.202001264.
   PubMed Web of Science ®Google Scholar
• Pigott, A. J.; Lepage, R. J.; White, J. M.; Coster, M. J. Total Synthesis of (±)-Nicolaioidesin B via a Highly Regio-and Diastereoselective Diels–Alder Reaction. Tetrahedron Lett. 2014, 55, 6864–6867. DOI: 10.1016/j.tetlet.2014.10.097.
   Web of Science ®Google Scholar
• Bañuelos, P.; García, J. M.; Gómez-Bengoa, E.; Herrero, A.; Odriozola, J. M.; Oiarbide, M.; Palomo, C.; Razkin, J. (1R)-(+)-Camphor and Acetone Derived Alpha’-Hydroxy Enones in Asymmetric Diels-Alder Reaction: catalytic Activation by Lewis and Brønsted Acids, Substrate Scope, Applications in Syntheses, and Mechanistic Studies. J. Org. Chem. 2010, 75, 1458–1473. DOI: 10.1021/jo9023039.
   PubMed Web of Science ®Google Scholar
• Seo, Y. H.; Damodar, K.; Kim, J.-K.; Jun, J.-G. Synthesis and Biological Evaluationof 2-Aroylbenzofurans, Rugchalcones A, B and Their Derivatives as Potent anti-Inflammatory Agents. Bioorg. Med. Chem. Lett. 2016, 26, 1521–1524. DOI: 10.1016/j.bmcl.2016.02.023.
   PubMed Web of Science ®Google Scholar
• Dudley, M. E.; Morshed, M. M.; Hossain, M. M. Convenient Preparation of 3-Ethoxycarbonyl Benzofurans from Salicylaldehydes and Ethyl Diazoacetate. Org. Synth. 2009, 86, 172–180. DOI: 10.1002/0471264229.os086.18.
   Google Scholar