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

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 05期

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.

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页码：867 / 870

页数：4

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