2018-02-012018-02-012016-01-261477-0520http://hdl.handle.net/2133/104895-Hydroxy-4-aryl-3,4-dihydro-1H-quinolin-2-ones are a small family of natural products isolated from fungal strains of Penicillium and Aspergillus. Most of its members, which are insecticides and anthelmintics, carry an isoprenoid C-6 side chain. The synthesis of a 6-propenyl-substituted advanced intermediate for the total synthesis of these natural products is presented in this paper. This was achieved through the stereoselective construction of a β,β-diarylacrylate derivative from 6-nitrosalicylaldehyde, using a Wittig olefination and a Heck–Matsuda arylation, followed by a selective Fe0-mediated reductive cyclization. Installation of the 6-propenyl side chain was performed by 5-O-allylation of the heterocycle, followed by Claisen rearrangement and conjugative migration of the allyl double bond, as the key steps. The Grubbs II-catalyzed olefin cross metathesis of the 6-allyl moiety with 2-methylbut-2-ene to afford a precursor of peniprequinolone is also reported.application/pdf2625 - 2636engopenAccessBioactive 6-substituted 5-hydroxy4-aryl-1H-quinolin-2-onesNatural ProductsMetathesisPrecursor of PeniprequinolonearticleRoyal Society of ChemistryUniversidad Nacional de RosarioSimonetti, Sebastián OsvaldoLarghi, Enrique LeandroKaufman, Teodoro Saúl