SEMINARIOS AREA QUÍMICA ORGÁNICA FBIOYF/IQUIR

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...