Total synthesis of LFA-1 antagonist BIRT-377 via organocatalytic asymmetric construction of a quaternary stereocenter
Total synthesis of LFA-1 antagonist BIRT-377 via organocatalytic asymmetric construction of a quaternary stereocenter
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DOI：
10.1021/ol047368b
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发表时间：
2005-03-03
期刊：
影响因子：
5.2
通讯作者：
Barbas, CF
中科院分区：
文献类型：
--
作者：
Chowdari, NS;Barbas, CF
本文报道了一条对映选择性全合成细胞粘附抑制剂BIRT-377的催化路线。通过L-脯氨酸衍生的、四唑催化的3-（4-溴苯基）-2-甲基丙烷与偶氮二甲酸二苄酯的直接不对称α-胺化反应，构建了四元立体中心。在这些研究的过程中，一锅三氟乙酰化/选择性苄氧羰基脱保护方法的开发。
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.