Lobato, RubénVeiga, Alberte X.Pérez-Vázquez, JaimeFernández-Nieto, FernandoPaleo Pillado, María RitaSardina López, Francisco Javier2018-07-092018-07-092013Lobato, R., Veiga, A., Pérez-Vázquez, J., Fernández-Nieto, F., Paleo, M., & Sardina, F. (2013). A One-Step, Versatile Synthesis of Dibenzo [n.2.2] Macrobicyclic Compounds via a Conformation-Directed Macrocyclization Reaction. Organic Letters, 15(16), 4090-4093. doi: 10.1021/ol40167671523-7060http://hdl.handle.net/10347/16985A 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 stepeng© 2013 American Chemical Societyjournal article10.1021/ol40167671523-7052open access