RT Journal Article
T1 A One-Step, Versatile Synthesis of Dibenzo [n.2.2] Macrobicyclic Compounds via a Conformation-Directed Macrocyclization Reaction
A1 Lobato, Rubén
A1 Veiga, Alberte X.
A1 Pérez-Vázquez, Jaime
A1 Fernández-Nieto, Fernando
A1 Paleo Pillado, María Rita
A1 Sardina López, Francisco Javier
AB 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
PB American Chemical Society
SN 1523-7060
YR 2013
FD 2013
LK http://hdl.handle.net/10347/16985
UL http://hdl.handle.net/10347/16985
LA eng
NO 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
NO This work was supported by the Ministerio de Economía y Competitividad of Spain (CTQ2011-22436) and Xunta de Galicia (PGIDIT10-PXIB209113PR, 10PXIB209155PR, and 2007/085)
DS Minerva
RD 28 abr 2026