12° SEMINARIO QUÍMICA ORGÁNICA IQUIR 2021

SEMINARIO QUÍMICA ORGÁNICA 02-08-21

EXPOSITOR: Dra. María Betina Comba

TÍTULO: "Efficient synthesis of antiviral agent uprifosbuvir enabled by new synthetic methods".

FUENTE: Artis Klapars, John Y. L. Chung, John Limanto,a Ralph Calabria,a Louis-Charles Campeau, a Kevin R. Campos, Wenyong Chen, Stephen M. Dalby, Tyler A. Davis, Daniel A. DiRocco, Alan M. Hyde,a Amude M. Kassim, Mona Utne Larsen, Guiquan Liu, Peter E. Maligres, Aaron Moment, Feng Peng, Rebecca T. Ruck, Michael Shevlin, Bryon L. Simmons, Zhiguo Jake Song, Lushi Tan, Timothy J. Wrighta and Susan L. Zultanski. Chem. Sci., 2021, 12, 9031-9036.

DÍA, HORA y LUGAR: Lunes 2 de agosto de 2021, 18:00 h, Plataforma MEET GOOGLE.

Link: meet.google.com/bfh-poxv-bso

RESUMEN: An efficient route to the HCV antiviral agent uprifosbuvir was developed in 5 steps from readily available uridine in 50% overall yield. This concise synthesis was achieved by development of several synthetic methods: (1) complexation-driven selective acyl migration/oxidation; (2) BSA-mediated cyclization to anhydrouridine; (3) hydrochlorination using FeCl3/TMDSO; (4) dynamic stereoselective phosphoramidation using a chiral nucleophilic catalyst. The new route improves the yield of uprifosbuvir 50-fold over the previous manufacturing process and expands the tool set available for synthesis of antiviral nucleotides.

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