title: Application of palladium-catalyzed carboxyl anhydride-boronic acid cross coupling in the synthesis of novel bile acids analogs with modified side chains.
abstract: Palladium-catalyzed cross coupling of 4-methoxycarbonyl phenyboronic acid with acetylated bile acids in which the carboxyl functions was activated by formation of a mixed anhydride with pivalic anhydride afforded the cross coupled compounds, which were converted in novel side chain modified bile acids by one pot carbonyl reduction/removal of the protecting acetyl groups by Wolff-Kishner reduction. Unambiguous assignments of the NMR signals and crystal characterization of the heretofore unknown compounds are provided.
authors.affiliation: Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510 México, D.F., Mexico.
authors.forename: Martha C
authors.initials: MC
authors.lastname: Mayorquín-Torres
authors.affiliation: Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510 México, D.F., Mexico.
authors.forename: Marcos
authors.initials: M
authors.lastname: Flores-Álamo
authors.affiliation: Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510 México, D.F., Mexico. Electronic address: martin.iglesias@unam.mx.
authors.forename: Martin A
authors.initials: MA
authors.lastname: Iglesias-Arteaga
mesh_terms: D000812:Anhydrides / Q000737:chemistry*; D001647:Bile Acids and Salts / Q000138:chemical synthesis* / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D008958:Models, Molecular; D008968:Molecular Conformation; D010165:Palladium / Q000737:chemistry*
chemical_list: D000812:Anhydrides; D001647:Bile Acids and Salts; D001897:Boronic Acids; D010165:Palladium
keywords: Boronic acids; NMR; Palladium-catalyzed cross coupling; Side chain modified bile acids; X-ray diffraction