27° SEMINARIO QUÍMICA ORGÁNICA IQUIR 2022

SEMINARIO QUÍMICA ORGÁNICA 28-11-22

EXPOSITOR: Lic. Nadia Martiren

TÍTULO: "Total Synthesis of the Dihydrooxepine-Spiroisoxazoline Natural Product Psammaplysin A".

FUENTE: Jan Paciorek, Denis Höfler, Kevin Rafael Sokol, Klaus Wurst, and Thomas Magauer J. Am. Chem. Soc. 2022, 144, 19704–19708.

DÍA, HORA y LUGAR: Lunes 28 de noviembre de 2022, 14:00 h

Modalidad virtual, Link: meet.google.com/hjn-ygro-twf (Plataforma MEET GOOGLE)

RESUMEN: We report a general synthetic entry to dihydrooxepine-spiroisoxazoline (DOSI) natural products that culminated in the first racemic total synthesis of psammaplysin A. For the synthesis of the unique spirocyclic fragment we employed a strategy that features two key transformations: (1) a diastereoselective Henry reaction/cyclization sequence to access the C7 hydroxylated isoxazoline scaffold in one step and (2) a regioselective Baeyer–Villiger ring expansion to install the fully substituted dihydrooxepine and avoid the risk of a previously observed oxepine-arene oxide rearrangement. The overall synthesis proceeds in 13 steps from an inexpensive starting material.

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