SEMINARIO QUÍMICA ORGÁNICA 13-4-26
EXPOSITOR: Lic. Darián Vazquez
TÍTULO: "Total syntheses of Tetrodotoxin and 9-epiTetrodotoxin".
FUENTE: Chen, P., Wang, J., Zhang, S. et al. Total syntheses of Tetrodotoxin and 9-epiTetrodotoxin. Nat Commun 15, 679 (2024). https://doi.org/10.1038/s41467-024-45037-0.
DÍA, HORA y LUGAR: Lunes 13 de abril de 2026, 14:00 h, virtual.
Modalidad virtual, Link: meet.google.com/wpi-ujuz-rok.
Resumen: Tetrodotoxin and congeners are specific voltage-gated sodium channel blockers that exhibit remarkable anesthetic and analgesic effects. Here, we present a scalable asymmetric syntheses of Tetrodotoxin and 9-epiTetrodotoxin from the abundant chemical feedstock furfuryl alcohol. The optically pure cyclohexane skeleton is assembled via a stereoselective Diels-Alder reaction. The dense heteroatom substituents are established sequentially by a series of functional group interconversions on highly oxygenated cyclohexane frameworks, including a chemoselective cyclic anhydride opening, and a decarboxylative hydroxylation. An innovative SmI2-mediated concurrent fragmentation, an oxo-bridge ring opening and ester reduction followed by an Upjohn dihydroxylation deliver the highly oxidized skeleton. Ruthenium catalyzed oxidative alkyne cleavage and formation of the hemiaminal and orthoester under acidic conditions enable the rapid assembly of Tetrodotoxin, anhydro-Tetrodotoxin, 9-epiTetrodotoxin, and 9-epi lactone-Tetrodotoxin.
Comentarios
Publicar un comentario