Total synthesis of LFA-1 antagonist BIRT-377 via organocatalytic asymmetric construction of a quaternary stereocenter.
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]
Chowdari
Naidu S
NS
The Skaggs Institute for Chemical Biology The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Barbas
Carlos F
CF
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
D000447:Aldehydes; C400461:BIRT 377; D048289:Imidazolidines; D016169:Lymphocyte Function-Associated Antigen-1