title: Pericyclic Cascade toward Isochromenes: Application to the Synthesis of Alkaloid Benzosimuline.
abstract: The synthesis of biologically active alkaloid benzosimuline, isolated from the shrub Zanthoxylum simulans, is reported. Key transformation involves an oxa-6π electrocyclic ring-opening/hetero-Diels-Alder pericyclic cascade. Although the last aromatization step proved to be cumbersome, this work unfolds a unique route to access interesting molecules from simple precursors.
authors.affiliation: Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET , Suipacha 531, S2002LRK Rosario, Argentina.
authors.forename: Martín J
authors.initials: MJ
authors.lastname: Riveira
authors.affiliation: Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET , Suipacha 531, S2002LRK Rosario, Argentina.
authors.forename: Agustina
authors.initials: A
authors.lastname: La-Venia
authors.affiliation: Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET , Suipacha 531, S2002LRK Rosario, Argentina.
authors.forename: Mirta P
authors.initials: MP
authors.lastname: Mischne
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D001578:Benzopyrans / Q000737:chemistry*; D061565:Cycloaddition Reaction; D013057:Spectrum Analysis / Q000379:methods; D013237:Stereoisomerism; D032106:Zanthoxylum / Q000737:chemistry
chemical_list: D000470:Alkaloids; D001578:Benzopyrans