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
Regioselective Synthesis of 3-Indolyl(alkoxy)acetates
Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor
Transesterifications mediated by t-BuNH2
Role of lipid peroxidation in biliary obstruction in the rat
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling
Synthesis of Bromoindole Alkaloids from Laurencia brongniartii