SEMINARIOS AREA QUÍMICA ORGÁNICA FBIOYF/IQUIR

SEMINARIO QUÍMICA ORGÁNICA 31-08-20 TÍTULO :  "Total Synthesis of Tagetitoxin" FUENTE :  Chi He, Hang Chu, Thomas P. Stratton, David Kossler, Kelly J. Eberle, Dillon T. Flood, and Phil S. Baran. J. Am. Chem. Soc. 2020 , 142 (32), 13683-13688. EXPOSITOR : Dr. Enrique L. Larghi DÍA, HORA y LUGAR : Lunes 31 de agosto de 2020, 18:00 h, Plataforma MEET GOOGLE. Link :  meet.google.com/bfh-poxv-bso RESUMEN : The intriguing structure of tagetitoxin ( 1 ), a longstanding challenge in natural product synthesis, has been the subject of multiple revisions and has been confirmed through total synthesis. The route commences from a renewable furan starting material and features a number of unusual transformations (such as rearrangements, bromocyclization, P(V)-based phosphate installation) to arrive at the target in 15 steps. As the route was designed to enable access to both enantiomers, the absolute configuration of the natural product could be assigned using a bioassay on (+)- 1 an...

SEMINARIO QUÍMICA ORGÁNICA 24-08-20 TÍTULO :  "Total synthesis of bryostatin 3" FUENTE :  Barry M. Trost, Youliang Wang, Andreas K. Buckl, Zhongxing Huang, Minh H. Nguyen, Olesya Kuzmina,  Science  2020 ,  368 , 1007-1011. EXPOSITOR : Dra. María I. Mangione DÍA, HORA y LUGAR : Lunes 24 de agosto de 2020, 18:00 h, Plataforma MEET GOOGLE. Link :  meet.google.com/kkr-rfrz-psv Link presentación : https://drive.google.com/file/d/1EuZRjpkuL1zmf0QgkCwJjFhc0v-DY8Ft/view?usp=sharing RESUMEN :  Las briostatinas son una familia de 21 productos naturales marinos complejos con un amplio rango de actividades biológicas potenciales. Entre las 21 briostatinas, briostatina 3 presenta la estructura más compleja. Mientras que 9 síntesis totales de briostatinas han sido logradas hasta la actualidad, briostatina 3 sólo ha sido obtenida una sola vez y su síntesis requiere un gran número de pasos (43 pasos en la secuencia lineal más larga y 88 pasos en total). En este artícu...

SEMINARIO QUÍMICA ORGÁNICA 10-08-20 TÍTULO : "Synthesis of Islatravir Enabled by a Catalytic, Enantioselective Alkynylation of a Ketone" FUENTE : Niki R. Patel, Christopher C. Nawrat, Mark McLaughlin, Yingju Xu, Mark A. Huffman, Hao Yang, Hongming Li, Aaron M. Whittaker, Teresa Andreani, François Lévesque, Anna Fryszkowska, Andrew Brunskill, David M. Tschaen, and Kevin M. Maloney. Organic Letters 2020 , 12 , 4659-4664.. EXPOSITOR : Lic. Carmela A. Crespo Guridi DÍA, HORA y LUGAR : Lunes 10 de agosto de 2020, 18:00 h, Plataforma MEET GOOGLE. Link : meet.google.com/pst-wjwm-pzs RESUMEN : The synthesis of the potent anti-HIV investigational treatment islatravir is described. The key step in this synthesis is a highly enantioselective catalytic asymmetric alkynylation of a ketone. This reaction is a rare example of the asymmetric addition of an alkyne nucleophile to a ketone through ligand-accelerated catalysis that was performed on a greater than 100 g scale. By leveraging a m...

SEMINARIO QUÍMICA ORGÁNICA 03-08-20 TÍTUL O : "Total Synthesis and Biological Evaluation of Tiancimycins A and B, Yangpumicin A, and Related Anthraquinone-Fused Enediyne Antitumor Antibiotics" FUENTE :  K. C. Nicolaou et al. J. Am. Chem. Soc. 2020 , 142 , 2549−2561. EXPOSITOR : Qco. Santiago Bolivar DÍA, HORA y LUGAR : Lunes 03 de agosto de 2020, 17:30 h, Plataforma MEET GOOGLE. Link : meet.google.com/ksi-cypi-pif LinkPresentación :  https://drive.google.com/file/d/1rniNOwHzP56xBLBp1Fg4cBJriLx9NJF3/view?ts=5f288ddf RESUMEN : The family of anthraquinone-fused enediyne antitumor antibiotics was established by the discovery of dynemicin A and deoxy- dynemicin A. It was then expanded, first by the isolation of uncialamycin, and then by the addition to the family of tiancimycins A−F and yangpumicin A. This family of natural products provides opportunities in total synthesis, biology, and medicine due to their novel and challenging molecular structures, intriguing biologica...

SEMINARIO QUÍMICA ORGÁNICA 27-07-20 TÍTUL O : "Enantioselective Diarylcarbene Insertion into Si-H Bonds Induced by Electronic Properties of the Carbenes" FUENTE :  Liang-liang Yang, Declan Evans, Bin Xu, Wen-Tao Li, Mao-Lin Li, Shou-Fei Zhu, K. N. Houk, and Qi-Lin Zhou   J. Am. Chem. Soc.  2020 ,  142 , 12394-12399, DOI :10.1021/jacs.0c04725. EXPOSITOR : Lic. Iván Cortés DÍA, HORA y LUGAR : Martes 28 de julio de 2020, 14 h, Plataforma MEET GOOGLE. Link :  meet.google.com/vod-ikcf-zzj RESUMEN : Catalytic enantioselection usually depends on differences in steric interactions between prochiral substrates and a chiral catalyst. We have discovered a carbene Si–H insertion in which the enantioselectivity depends primarily on the electronic characteristics of the carbene substrate, and the log(er) values are linearly related to Hammett parameters. A new class of chiral tetraphosphate dirhodium catalysts was developed; it shows excellent activity and enantioselecti...

SEMINARIO QUÍMICA ORGÁNICA 29-06-20 TÍTULO :  "Desarrollo y aplicación de un modelo de clasificación de reacciones basado en datos" FUENTE : (a)  Ghiandoni, G. M.; Bodkin, M. J.; Chen, B.; Hristozov, D.; Wallace, J. E. A.; Webster, J.; Gillet, V. J. J. Chem. Inf. Model.   2019 , 59 , 4167. (b) Ghiandoni, G. M.; Bodkin, M. J.; Chen, B.; Hristozov, D.; Wallace, J. E. A.; Webster, J.; Gillet, V. J. J. Comput.-Aided Mol. Des.  2020 , 34 , 783. EXPOSITOR : Lic. Natalia Labadie DÍA, HORA y LUGAR : Lunes 29 de junio de 2020, 14 h, Plataforma MEET GOOGLE. Link :  meet.google.com/ksi-cypi-pif Link Presentación:   https://drive.google.com/file/d/1KpSICatGlVNWpFuZ92Hbvw-0nCwXWata/view?usp=sharing RESUMEN : La clasificación de reacciones es considerada una tarea importante para múltiples aplicaciones y tradicionalmente fue lograda a través de métodos basados en reglas descritas a mano. Sin embargo, la disponibilidad de grandes colecciones de reacciones habilita...

SEMINARIO QUÍMICA ORGÁNICA 22-06-20 TÍTULO : "Divergent Total Synthesis of Chaetoglines C to F" FUENTE : Shi,Y ; Xu,Z ; Tan, R, Lei, X. J. Org. Chem. 2019 , 84 , 8766-8770. EXPOSITOR : Lic. Elida Thobokholt DÍA, HORA y LUGAR : Lunes 22 de junio de 2020, 14 h, Plataforma MEET GOOGLE. Link : meet.google.com/ksi-cypi-pif RESUMEN : The first total syntheses of chaetoglines C-F via a bioinspired and divergent synthetic strategy are reported. Chaetoglines C and D were obtained from the condensation of hemiacetal and tryptophan methyl ester building blocks followed by functional group transformations. The synthesis of chaetogline E employed the diastereoselective Pictet- Spengler reaction, and the tetrahydro-carboline skeleton was further utilized as a precursor for an oxidative aromatization reaction to introduce the β-carboline moiety of chaetogline F.