title: Total synthesis of LFA-1 antagonist BIRT-377 via organocatalytic asymmetric construction of a quaternary stereocenter.
abstract: A catalytic route for enantioselective total synthesis of cell adhesion inhibitor BIRT-377 is described. The quaternary stereocenter was constructed through l-proline-derived, tetrazole-catalyzed direct asymmetric alpha-amination of 3-(4-bromophenyl)-2-methylpropanal with dibenzyl azodicarboxylate. In the course of these studies, a one-pot trifluoro acetylation/selective benzyloxycarbonyl deprotection method was developed. [structure: see text]
authors.affiliation: The Skaggs Institute for Chemical Biology The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
authors.forename: Naidu S
authors.initials: NS
authors.lastname: Chowdari
authors.forename: Carlos F
authors.initials: CF
authors.lastname: Barbas
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D002448:Cell Adhesion / Q000187:drug effects; D048289:Imidazolidines / Q000138:chemical synthesis*; D016169:Lymphocyte Function-Associated Antigen-1 / Q000187:drug effects; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; C400461:BIRT 377; D048289:Imidazolidines; D016169:Lymphocyte Function-Associated Antigen-1