Chowdari Naidu S, Barbas Carlos F
The Skaggs Institute for Chemical Biology The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Org Lett. 2005 Mar 3;7(5):867-70. doi: 10.1021/ol047368b.
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]
描述了一种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3-(4-溴苯基)-2-甲基丙醛与二苄基偶氮二甲酸酯的直接不对称α-胺化反应构建了季碳立体中心。在这些研究过程中，开发了一种一锅法三氟乙酰化/选择性苄氧羰基脱保护方法。[结构：见原文]
