2023-08-112023-08-112023-06-272470-1343http://hdl.handle.net/2133/26175An efficient and straightforward route toward the isatin-type natural product melosatin A is reported, employing a trisubstituted aniline as a key intermediate. The latter was synthesized in 4 steps and 60% overall yield from eugenol, through its regioselective nitration, sequentially followed by a Williamson methylation, an olefin cross-metathesis with 4-phenyl-1-butene and the simultaneous reduction of olefin and nitro groups. The final step, a Martinet cyclocondensation of the key aniline with diethyl 2-ketomalonate, provided the natural product with 68% yield.application/pdf23174-23181engopenAccessIsatinIn vitro studiesTetraethylene glycolpublishedVersionBolivar Ávila, Santiago J.Ledesma, Gabriela N.Kaufman, Teodoro SaúlTestero, Sebastián A.Larghi, Enrique LeandroUniversidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y FarmacéuticasAttribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0)