Total synthesis of LFA-1 antagonist BIRT-377 via organocatalytic asymmetric construction of a quaternary stereocenter

被引:148
作者
Chowdari, NS
Barbas, CF
机构
[1] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[3] Scripps Res Inst, Dept Biol Mol, La Jolla, CA 92037 USA
关键词
D O I
10.1021/ol047368b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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-methylpropanaI with dibenzyl azodicarboxylate. In the course of these studies, a one-pot trifluoro acetylation/selective benzyloxycarbonyl deprotection method was developed.
引用
收藏
页码:867 / 870
页数:4
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