SEMINARIOS AREA QUÍMICA ORGÁNICA FBIOYF/IQUIR

SEMINARIO QUÍMICA ORGÁNICA 05-10-20 EXPOSITOR : Qco. Juan  Ramos TÍTULO : "Cicloadición [2+2] de alenos" FUENTE :  Johannes. M. Wiest, Michael L. Conner, and M. Kevin Brown, Allenoates in Enantioselective [2+2] Cycloadditions: From a Mechanistic Curiosity to a Stereospecific Transformation, J. Am. Chem. Soc. 2018 , 140 , 15943−15949. DÍA, HORA y LUGAR : Lunes 5 de octubre de 2020, 18:00 h, Plataforma MEET GOOGLE. Link :  meet.google.com/bfh-poxv-bso RESUMEN :  Identification of a novel catalyst−allenoate pair allows enantioselective [2+2] cycloaddition of α-methylstyrene. To understand the origin of selectivity, a detailed mechanistic investigation was conducted. Herein, two competing reaction pathways are proposed, which operate simultaneously and funnel the alkenes to the same axially chiral cyclobutanes. In agreement with the Woodward− Hoffmann rules, this mechanistic curiosity can be rationalized through a unique symmetry operation that was elucidated by deuterat...

SEMINARIO QUÍMICA ORGÁNICA 28-09-20 TÍTULO : "Síntesis de péptidos bioactivos químicamente modificados: avances recientes y desafíos para la química medicinal" FUENTE :  - Gracia SR, Gaus K, Sewald N. Synthesis of chemically modified bioactive peptides: recent advances, challenges and developments for medicinal chemistry. Future Med Chem. 2009 Oct;1(7):1289-310. doi:  https://doi.org/10.4155/fmc.09.97 - Jolene L. Lau, Michael K. Dunn, Therapeutic peptides: Historical perspectives, current development trends, and future directions, Bioorganic & Medicinal Chemistry , Volume 26, Issue 10, 2018 , Pages 2700-2707, ISSN 0968-0896, https://doi.org/10.1016/j.bmc.2017.06.052 . - Li H, Aneja R, Chaiken I. Click chemistry in peptide-based drug design. Molecules . 2013 Aug 16;18(8):9797-817. doi: 10.3390/molecules18089797. PMID: 23959192; PMCID: PMC4155329. - Kevin L. Bicker and Steven L. Cobb, Chem. Commun. , 2020 , 56, 11158-11168, https://doi.org/10.1039/D0CC04704J EXPOSITOR : Li...

SEMINARIO QUÍMICA ORGÁNICA 21-09-20 TÍTULO :  " Total Synthesis of ( -)-Daphnezomines A and B " FUENTE :  Guangpeng Xu, Jinbao Wu, Luyang Li, Yunan Lu, Chao Li.  J. Am. Chem. Soc .  2020 ,  142 , 36, 15240–15245 . EXPOSITOR : Lic. Nadia L. Martiren DÍA, HORA y LUGAR : Lunes 21 de septiembre de 2020, 18:00 h, Plataforma MEET GOOGLE. Link :  meet.google.com/bfh-poxv-bso RESUMEN :   Daphnezomines A and B are structurally unusual Daphniphyllum alkaloids that contain a unique aza-adamantane core skeleton. Herein, a modular approach to these alkaloids is presented that exploits a diverse array of reaction strategies. Commencing from a chiral pool terpene–( S )-carvone, the azabicyclo[3.3.1]nonane backbone, which occurs widely in Daphniphyllum alkaloids, was easily accessed through a Sharpless allylic amination and a palladium-catalyzed oxidative cyclization. A protecting group enabled a stereoselective B -alkyl Suzuki-Miyaura coupling sequence, and an Fe...

SEMINARIO QUÍMICA ORGÁNICA 14-09-20 TÍTULO :  " Enantioselective Total Synthesis of (+)-Corymine and (−)-Deformylcorymine " FUENTE :  Benxiang Zhang, Xiaoqing Wang, and Chaozhong Li.  J. Am. Chem. Soc . 2020 , 142, 3269−3274. EXPOSITOR : Dra. Andrea B. J. Bracca DÍA, HORA y LUGAR : Lunes 14 de septiembre de 2020, 18:00 h, Plataforma MEET GOOGLE. Link :  meet.google.com/bfh-poxv-bso RESUMEN : We report herein the first enantioselective total synthesis of akuammiline alkaloids (+)-corymine and (−)-deformylcorymine. Starting from commercially available N-nosyltryptamine, the target molecules are both achieved in 11 steps. Key elements of the design include (a) a copper-catalyzed enantioselective addition of dimethyl malonate to a 3-bromooxindole to secure the C7 all-carbon quaternary stereocenter, (b) a one-step construction of cyclohexyl and pyrrolidinyl rings via intramolecular nucleophilic C- and N-addition, and (c) a nickel-promoted 7-endo cyclization of alkenyl br...

SEMINARIO QUÍMICA ORGÁNICA 07-09-20 TÍTULO :  " Importancia de las redes de colaboración para la generación de nuevos tratamientos de enfermedades. Desarrollo del compuesto candidato SK3186899/DDD853651 para el tratamiento de Leishmaniasis visceral " FUENTE :  www.dndi.org. Reporte del DNDi del 2019. M. G. Thomas et al (P. G. Wyatt*, K. D. Read* and T. J. Miles*). Identification of GSK3186899/DDD853651 as a Preclinical Development Candidate for the Treatment of Visceral Leishmaniasis. J. Med. Chem . 2019 , 62, 3, 1180–1202. https://doi.org/10.1021/acs.jmedchem.8b01218 . EXPOSITOR : Lic. Alejandro Recio Balsells DÍA, HORA y LUGAR : Lunes 7 de septiembre de 2020, 18:00 h, Plataforma MEET GOOGLE. Link :  meet.google.com/bfh-poxv-bso RESUMEN :  La sinergia que producen las redes de colaboración entre la industria farmacéutica, el sector académico, ONG y el sector gubernamental es fundamental para la generación de nuevos tratamientos de enfermedades, en especial para la...

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...