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
Transesterifications mediated by t-BuNH2
Trapping enols of esters and lactones with diazomethane
The absoluteconfiguration of cuauhtemone and related compounds
First Total Synthesis of ()-Flustraminol B
Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea
Role of lipid peroxidation in biliary obstruction in the rat
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling