Preparation of (+)- and (?)- ?-phenyl- and ?-(4-chlorophenyl)-?- butyrolactones: Key Intermediates in the Synthesis of ?-phenyl-GABA and Baclofen.
Suárez Castillo, Oscar Rodolfo
2016
Jazmín Gómez-Gutiérrez, Myriam Meléndez-Rodríguez,* Óscar R. Suárez-Castillo, Luis E. CastelánDuarte, Manuel J. Fragoso-Vázquez, Erick López-Vázquez, and Maricruz Sánchez-Zavala. Preparation of (+)- and (?)- ?-phenyl- and ?-(4-chlorophenyl)-?- butyrolactones: Key Intermediates in the Synthesis of ?-phenyl-GABA and Baclofen. J. Mex. Chem. Soc. 2015, 59(1), 12-18.
Abstract
The preparation of ?-phenyl- and ?-(4-chlorophenyl)-?-butyrolactones ( )-3 and ( )-4 and their resolution to the corresponding (+)-(S)-3, (?)-(R)-3 and (+)-(S)-4, (?)-(R)-4 through formation, flash column chromatography separation and subsequent hydrolysis of diastereoisomeric 4-hydroxybutyramides (2?R,3S)-5, (2?R,3R)-5, (2?R,3S)-6 and (2?R,3R)-6 is described. The absolute configuration assignment of enantiopure 3 and 4 was supported by X-ray crystallographic structures of (2?R,3R)-5, (2?R,3S)-6 and (2?R,3R)-6
Artículos relacionados
Synthesis of Indolylindolines Mediated by tert-BuNH2
First Total Synthesis of ()-Flustraminol B
13C NMR and crystallographic evidence of push-pull effects in furoindolic ?-enamino esters
Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling