2° SEMINARIO QUIMICA ORGANICA IQUIR 2020

SEMINARIO QUÍMICA ORGÁNICA 13-04-20
TÍTULO: "Formal Total Synthesis of Pericoannosin A ".

EXPOSITOR: Qco. Msc. Javier Cala.
DÍA, HORA y LUGAR: Lunes 13 de abril de 2020, 14 h, Plataforma ZOOM.

FUENTE: Mark G. Fulton, Jeanette L. Bertron, Carson W. Reed and Craig W. Lindsley, J. Org. Chem. 2019, 84, 18, 12187-12191. DOI:10.1021/acs.joc.9b01846

ABSTRACT: A concise formal total synthesis of pericoannosin A, by the synthesis of an advanced intermediate of pericoannosin A, was achieved in eight steps from commercially available isoprene in a 21.7% overall yield. Key transformations for this expedited route include an enantioselective organocatalytic Diels–Alder reaction to construct the C ring, a diastereoselective reduction (under Felkin–Ahn control), and a hydroboration/oxidation sequence for chain homologation. This work represents the second synthetic effort toward pericoannosin A, the only reported natural product based on a hexahydro-1H-isochromen-5-isobutylpyrrolidin-2-one core.

PPT: https://drive.google.com/open?id=1XzgOBJsFQGyWxwFoTLWjNZnB88G8rxpf

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