SEMINARIOS AREA QUÍMICA ORGÁNICA FBIOYF/IQUIR

  SEMINARIO QUÍMICA ORGÁNICA 6-12-21 EXPOSITOR : Qco. Juan M. Ramos M. TÍTULO :  " Unified Synthesis of Polycyclic Alkaloids by Complementary Carbonyl Activation " . FUENTE : Guoli He, Benjamin List,* and Mathias Christmann*, Angew. Chem. Int. Ed. 2021 , 60 , 13591–13596. DÍA, HORA y LUGAR : Lunes 6 de diciembre de 2021, 18:00 h, Plataforma MEET GOOGLE. Link :  meet.google.com/bfh-poxv-bso RESUMEN :  A complementary dual carbonyl activation strategy for the synthesis of polycyclic alkaloids has been developed. Successful applications include the synthesis of tetracyclic alkaloids harmalanine and harmalacinine, pentacyclic indoloquinolizidine alkaloid nortetoyobyrine, and octacyclic bcarboline alkaloid peganumine A. The latter synthesis features a protecting-group-free assembly and an asymmetric disulfonimide-catalyzed cyclization. Furthermore, formal syntheses of hirsutine, deplancheine, 10-desbromoarborescidine A, and oxindole alkaloids rhynchophylline and isorhy...

SEMINARIO QUÍMICA ORGÁNICA 29-11-21 EXPOSITOR :   Lic. Nadia L. Martiren TÍTULO :  " Enantioselective Total Synthesis of (+)-Heilonine " . FUENTE :   Kyle J. Cassaidy and Viresh H. Rawal,   J. Am. Chem. Soc. 2021 , 143 , 16394-16400. DÍA, HORA y LUGAR : Lunes 29 de noviembre de 2021, 18:00 h, Plataforma MEET GOOGLE. Link :  meet.google.com/bfh-poxv-bso RESUMEN : Chemical transformations that rapidly and efficiently construct a high level of molecular complexity in a single step are perhaps the most valuable in total synthesis. Among such transformations is the transition metal catalyzed [2 + 2 + 2] cycloisomerization reaction, which forges three new C–C bonds and one or more rings in a single synthetic operation. We report here a strategy that leverages this transformation to open de novo access to the Veratrum family of alkaloids. The highly convergent approach described herein includes (i) the enantioselective synthesis of a diyne fragment containing the ster...

SEMINARIO QUÍMICA ORGÁNICA 08-11-21 EXPOSITOR :   Lic. Alejandro Recio Balsells TÍTULO :  " Fexinidazol el primer tratamiento completamente oral para la enfermedad del sueño " . FUENTE :   1-https://dndi.org/press-releases/2021/us-fda-approves-fexinidazole-as-first-all-oral-treatment-sleeping-sickness/  2- Trop. Med. Infect. Dis. 2020 , 5(1), 17; doi: 10.3390/tropicalmed5010017 )  3- Bioorg Med Chem Lett. 2011 ; 21(3):1015-8. doi: 10.1016/j.bmcl.2010.12.040.  4- J. Org. Chem. 2015 , 80, 21, 10498–10504; doi: 10.1021/acs.joc.5b02133. DÍA, HORA y LUGAR : Lunes 8 de noviembre de 2021, 17:00 h, Plataforma MEET GOOGLE. Link :  meet.google.com/bfh-poxv-bso RESUMEN :   Recientemente la FDA ha aprobado el uso de Fexinidazol para el tratamiento de la Tripanosomiasis Humana Africana en sus dos estadios. Este desarrollo es de suma importancia debido a que el tratamiento es completamente oral, reemplazando tratamientos previos en los cuales era necesario ...

SEMINARIO QUÍMICA ORGÁNICA 01-11-21 EXPOSITOR :   Lic. Carmela A. Crespo Guridi TÍTULO :  " Concise Total Synthesis of Peyssonnoside A " . FUENTE :   Gleb A. Chesnokov and Karl Gademann. J. Am. Chem. Soc. 2021 , 143 , 14083−14088.DOI: https://doi.org/10.1021/jacs.1c07135 DÍA, HORA y LUGAR : Lunes 1 de noviembre de 2021, 18:00 h, Plataforma MEET GOOGLE. Link :  meet.google.com/bfh-poxv-bso RESUMEN : Peyssonnoside A is a marine-derived sulfated diterpenoid glucoside with a unique 5/6/3/6 tetracyclic skeleton with a highly substituted cyclopropane ring deeply embedded into the structure. Herein, we report the first total synthesis of this natural product in a concise, efficient, scalable, and highly diastereoselective fashion. The aglucone peyssonnosol was synthesized in 21% overall yield after 15 steps, featuring a Simmons−Smith cyclopropanation and Mukaiyama hydration, fully controlled by the spatial structure of the substrates.

SEMINARIO QUÍMICA ORGÁNICA 25-10-21 EXPOSITOR :   Dra. Silvina C. Pellegrinet TÍTULO :  " Taming Radical Pairs in the Crystalline Solid State: Discovery and Total Synthesis of Psychotriadine " . FUENTE :   Jordan J. Dotson, Ieva Liepuoniute, J. Logan Bachman, Vince M. Hipwell, Saeed I. Khan, K. N. Houk,* Neil K. Garg,* and Miguel A. Garcia-Garibay*. J. Am. Chem. Soc. 2021, 143, 4043-4054. https://doi.org/10.1021/jacs.1c01100 DÍA, HORA y LUGAR : Lunes 25 de octubre de 2021, 18:00 h, Plataforma MEET GOOGLE. Link :  meet.google.com/bfh-poxv-bso RESUMEN : Solid-state photodecarbonylation is an attractive but underutilized methodology to forge hindered C−C bonds in complex molecules. This study discloses the use of this reaction to assemble the vicinal quaternary stereocenter motif present in bis(cyclotryptamine) alkaloids. Our strategy was enabled by experimental and computational investigations of the role of substrate conformation on the success or failure of the soli...

SEMINARIO QUÍMICA ORGÁNICA 18-10-21 EXPOSITOR :   Qco. Santiago J. Bolivar Avila TÍTULO :  " Scalable Asymmetric Syntheses of Foslevodopa and Foscarbidopa Drug Substances for the Treatment of Parkinson’s Disease " . FUENTE :   Alexander D. Huters, James Stambuli, Russell C. Klix, Mark A. Matulenko, Vincent S. Chan, Justin Simanis, David R. Hill,* Rajarathnam E. Reddy, Timothy B. Towne, John R. Bellettini, Brian J. Kotecki, Benoit Cardinal-David, Jianguo Ji, Eric A. Voight, Minshan Shou, Selvakumar Balaraman, Abhishek Ashok, and Soma Ghosh .  J. Org. Chem.   2021 ,  ASAP .  DOI: https://doi.org/10.1021/acs.joc.1c00905 . DÍA, HORA y LUGAR : Lunes 18 de octubre de 2021, 18:00 h, Plataforma MEET GOOGLE. Link :  meet.google.com/bfh-poxv-bso RESUMEN : Foslevodopa (FLD, levodopa 4′-monophosphate, 3) and foscarbidopa (FCD, carbidopa 4′-monophosphate, 4) were identified as water-soluble prodrugs of levodopa (LD, 1) and carbidopa (CD, 2), respectively, wh...

SEMINARIO QUÍMICA ORGÁNICA 04-10-21 EXPOSITOR :  Lic. Iván Cortés TÍTULO :  " The Total Synthesis of (−)-Scabrolide A " . FUENTE :   Nicholas J. Hafeman, Steven A. Loskot, Christopher E. Reimann, Beau P. Pritchett, Scott C. Virgil, and Brian M. Stoltz. J. Am. Chem. Soc. 2020 , 142 , 8585−8590.  DOI: https://dx.doi.org/10.1021/jacs.0c02513 . DÍA, HORA y LUGAR : Lunes 4 de octubre de 2021, 18:00 h, Plataforma MEET GOOGLE. Link :  meet.google.com/bfh-poxv-bso RESUMEN :  The first total synthesis of the norcembranoid diterpenoid scabrolide A is disclosed. The route begins with the synthesis of two chiral pool-derived fragments, which undergo a convergent coupling to expediently introduce all 19 carbon atoms of the natural product. An intramolecular Diels–Alder reaction and an enone–olefin cycloaddition/fragmentation sequence are then employed to construct the fused [5–6–7] linear carbocyclic core of the molecule and complete the total synthesis.