1° SEMINARIO QUÍMICA ORGÁNICA IQUIR 2022

SEMINARIO QUÍMICA ORGÁNICA 04-04-22

EXPOSITOR: Dr. Didier Farley Vargas Vargas

TÍTULO: "Total Synthesis of the Acetyl CoA Carboxylase Inhibitor Soraphen A: Asymmetric Tsuji Reduction Enables Successive Olefin Metathesis".

FUENTE:  Schempp, T. T. and Krische, M. J. J. Am. Chem. Soc. 2022, 144, 1016–1022.

DÍA, HORA y LUGAR: Lunes 4 de abril de 2022, 18:00 h, Plataforma MEET GOOGLE.

Link: meet.google.com/bfh-poxv-bso

RESUMEN: The total synthesis of soraphen A, a myxobacterial metabolite and inhibitor of acetyl CoA carboxylase, was completed in 11 steps (longest linear sequence), less than half the steps previously required. Seven metal-catalyzed processes were deployed to unlock step-economy (comprising five asymmetric processes and four C–C bond formations). The present route does not utilize chiral auxiliaries, and four of five C–C bond formations exploit non-premetalated partners. To maximize convergency, an asymmetric Tsuji reduction was developed using a Pd-AntPhos catalyst that allows a metathesis-inactive allylic carbonate to serve as a masked terminal olefin, thereby enabling successive olefin metathesis events.