title: Total Syntheses of Aporphine Alkaloids via Benzyne Chemistry: An Approach to the Formation of Aporphine Cores.
abstract: Total syntheses of lysicamine, (±)-nuciferine, (±)-nornuciferine, (±)-zanthoxyphylline iodide, (±)-O-methylisothebaine, and (±)-trimethoxynoraporphine were accomplished by an approach that involves the formation of aporphine cores through reactions between an isoquinoline derivative and silylaryl triflates promoted by CsF. Unprecedented formations of aporphine cores proceeded in good yields presumably through [4 + 2] cycloaddition reactions followed by hydrogen migrations.
authors.affiliation: Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo , Diadema, SP, Brazil.
authors.forename: Allan F C
authors.initials: AF
authors.lastname: Rossini
authors.affiliation: Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo , Diadema, SP, Brazil.
authors.forename: Ana Carolina A
authors.initials: AC
authors.lastname: Muraca
authors.affiliation: Instituto de Química, Universidade Federal de Mato Grosso do Sul , Campo Grande, MS, Brazil.
authors.forename: Gleison A
authors.initials: GA
authors.lastname: Casagrande
authors.affiliation: Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo , Diadema, SP, Brazil.
authors.forename: Cristiano
authors.initials: C
authors.lastname: Raminelli
mesh_terms: D001060:Aporphines / Q000138:chemical synthesis* / Q000737:chemistry; D001555:Benzene Derivatives / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure
chemical_list: D001060:Aporphines; D001555:Benzene Derivatives; C524146:benzyne