21° SEMINARIO QUÍMICA ORGÁNICA IQUIR 2020

 SEMINARIO QUÍMICA ORGÁNICA 26-10-20

EXPOSITOR: Dr. Didier Farley Vargas Vargas

TÍTULO: "Total Syntheses of Xiamycins A, C, F, H and Oridamycin A and Preliminary Evaluation of their Anti-Fungal Properties"

FUENTE: Pfaffenbach, M., Bakanas, I., O'Connor, N. R., Herrick, J. L. and Sarpong, R. Angew. Chem. Int. Ed. 2019, 58, 15304 –15308.

DÍA, HORA y LUGAR: Lunes 26 de octubre de 2020, 18:00 h, Plataforma MEET GOOGLE.

Link: meet.google.com/bfh-poxv-bso

RESUMEN: Divergent and enantiospecific total syntheses of the indolosesquiterpenoids xiamycins A, C, F, H and oridamycin A have been accomplished. The syntheses, which commence from (R)-carvone, employ a key photoinduced benzannulation sequence to forge the carbazole moiety characteristic of these natural products. Late-stage diversification from a common intermediate enabled the first syntheses of xiamycins C and F, and an unexpected one-pot oxidative decarboxylation, which may prove general, led to xiamycin H. All synthetic intermediates and the natural products were tested for anti-fungal activity. Xiamycin H emerged as an inhibitor of three agriculturally relevant fungal pathogens.