title: A one-step, versatile synthesis of dibenzo [n.2.2] macrobicyclic compounds via a conformation-directed macrocyclization reaction.
abstract: A series of dibenzo [n.2.2] bicyclic compounds (n = 2-20) were prepared in one step and good yields starting from dimethyl anthracene-9,10-dicarboxylate. Reduction of the aromatic diester using lithium/naphthalene led to a bis-enolate that was cyclized with a variety of bis-electrophiles. The ease of the cyclization is probably due to the puckered conformation of the intermediate formed after the first alkylation step, in which the newly introduced chain that will become the bridge portion occupies a pseudoaxial position, positioning the leaving group close to the enolate nucleophile in the macrocyclization step.
authors.affiliation: Departamento de Química Orgánica and Centro Singular de Investigación en Química Biológica y Materiales Moleculares, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain.
authors.forename: Rubén
authors.initials: R
authors.lastname: Lobato
authors.forename: Alberte X
authors.initials: AX
authors.lastname: Veiga
authors.forename: Jaime
authors.initials: J
authors.lastname: Pérez-Vázquez
authors.forename: Fernando
authors.initials: F
authors.lastname: Fernández-Nieto
authors.forename: M Rita
authors.initials: MR
authors.lastname: Paleo
authors.forename: F Javier
authors.initials: FJ
authors.lastname: Sardina