A One-Step, Versatile Synthesis of Dibenzo [n.2.2] Macrobicyclic Compounds via a Conformation-Directed Macrocyclization Reaction

作者：Lobato Ruben; Veiga Alberte X; Perez Vazquez Jaime; Fernandez Nieto Fernando; Rita Paleo M; Javier Sardina F

来源：Organic Letters, 2013, 15(16): 4090-4093.

DOI：10.1021/ol4016767

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.

• 出版日期2013-8-16