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

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• 作者：Rub茅n Lobato ; Alberte X. Veiga ; Jaime P茅rez-V谩zquez ; Fernando Fern谩ndez-Nieto ; M. Rita Paleo ; F. Javier Sardina
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：August 16, 2013
• 年：2013
• 卷：15
• 期：16
• 页码：4090-4093
• 全文大小：255K
• 年卷期：v.15,no.16(August 16, 2013)
• ISSN：1523-7052

文摘

A series of dibenzo [n.2.2] bicyclic compounds (n = 2鈥?0) 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.