来自二基的序列C-Si键形成:适用于西兰二醇异前体的应用
Lone Nielsen1, Troels Skrydstrup
1Center for Insoluble Protein Structures, Department of Chemistry, and Interdisciplinary Nanoscience Center, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark.
Journal of the American Chemical Society
|September 5, 2008
概括
研究人员开发了一种新的两步合成,用于西兰二醇异,关键的蛋白酶抑制剂. 这种方法有效地创建碳-键,使得这些重要的化合物可以获得.
科学领域:
- 有机化学 有机化学
- 药用化学 医学化学
- 生物化学 生物化学
背景情况:
- 西兰二醇异质体显示出作为蛋白质分解酶抑制剂的高活性.
- 越来越多的兴趣需要这些化合物的高效合成途径.
- 对于含有西兰的二片段,需要进行一般和直接的合成接入.
研究的目的:
- 报告一种两步方法,用于组装含有西兰的二片段的碳骨干.
- 通过化学选择性歧视实现二基的顺序功能化.
- 为提供对西兰二醇异的一般和直接合成接入.
主要方法:
- 使用激素启动器或威尔金森催化剂对二基的基化,形成一个基.
- 用金属减少基基,以产生基试剂.
- 对光学活跃的 tert-butanesulfinimine 添加了 silyl 试剂,以形成第二个 C-Si 键.
主要成果:
- 一个含有西兰的二片段的成功两步合成.
- 通过顺序功能化,有效地创建两个碳-键.
- 在添加 tert-butanesulfinimine 的过程中,获得了高的 diastereoselectivity.
- 在diphenylsilane中证明了两种化物的化学选择性歧视.
结论:
- 开发的方法提供了对西兰二醇异的一般和直接合成接入.
- 这种方法允许控制和高效合成不寻常的蛋白酶抑制剂.
- 顺序功能化策略是获得这些有价值化合物的关键.
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