23° SEMINARIO QUÍMICA ORGÁNICA IQUIR 2021

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.

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