A One-Step, Versatile Synthesis of Dibenzo [n.2.2] Macrobicyclic Compounds via a Conformation-Directed Macrocyclization Reaction
Por favor, use este identificador para citas ou ligazóns a este ítem:
http://hdl.handle.net/10347/16985
Ficheiros no ítem
Metadatos do ítem
Título: | A One-Step, Versatile Synthesis of Dibenzo [n.2.2] Macrobicyclic Compounds via a Conformation-Directed Macrocyclization Reaction |
Autor/a: | Lobato, Rubén Veiga, Alberte X. Pérez-Vázquez, Jaime Fernández-Nieto, Fernando Paleo, M. Rita Sardina, F. Javier |
Centro/Departamento: | Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares Universidade de Santiago de Compostela. Departamento de Química Orgánica |
Data: | 2013 |
Editor: | American Chemical Society |
Cita bibliográfica: | Lobato, 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/ol4016767 |
Resumo: | 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 |
Versión do editor: | https://doi.org/10.1021/ol4016767 |
URI: | http://hdl.handle.net/10347/16985 |
DOI: | 10.1021/ol4016767 |
ISSN: | 1523-7060 |
E-ISSN: | 1523-7052 |
Dereitos: | © 2013 American Chemical Society |
Coleccións
-
- CIQUS-Artigos [475]
- QO-Artigos [436]