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首页> 外文期刊>Chemistry: A European journal >Synthesis of small molecules with high scaffold diversity: Exploitation of metathesis cascades in combination with inter-and intramolecular diels-alder reactions
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Synthesis of small molecules with high scaffold diversity: Exploitation of metathesis cascades in combination with inter-and intramolecular diels-alder reactions

机译：合成具有高支架多样性的小分子：结合分子间和分子间狄尔斯-阿尔德反应的复分解级联反应的开发

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摘要

Our knowledge of the biological relevance of regions of chemical space is shaped, in large part, by the synthetic accessibility of small molecules.Historically, however, chemists have explored chemical space in an exceptionally uneven and unsystematic way. We have previously demonstrated that metathesis cascade chemistry may be harnessed to yield small molecule collections with high scaffold diversity. Here, we describe the extent to which inter- and intramolecular Diels-Alder reactions, when used in conjunction with metathesis cascades, can extendthe range of molecular scaffolds that are accessible. A range of metathesis substrates was prepared from combinations of two or three building blocks. Metathesis cascades were exploited to "reprogram" the molecular scaffolds. In many cases, the metathesis products were 1,3-dienes, which were potential substrates for either inter- or intramolecular Diels-Alder reactions. The synthesis and functionalisation of the products was often facilitated by fluorous tagging, for example by using a "safety-catch" linker that we have developed. It was demonstrated that, incertain cases, Diels-Alder reactions could extend the range of molecular scaffolds that may be prepared by using metathesis cascade reactions.
机译：我们对化学空间区域生物学相关性的了解在很大程度上取决于小分子的合成可及性，但是从历史上看，化学家们以一种极其不平衡且非系统的方式探索了化学空间。我们以前已经证明，复分解级联化学可以利用以产生具有高支架多样性的小分子集合。在这里，我们描述了分子间和分子内Diels-Alder反应与易位级联结合使用时可扩展分子支架范围的程度。由两个或三个构件的组合制备了一系列复分解底物。利用复分解级联来“重编程”分子支架。在许多情况下，复分解产物是1,3-二烯，是分子间或分子内Diels-Alder反应的潜在底物。氟标记通常有助于产品的合成和功能化，例如使用我们开发的“安全捕获”连接子。结果表明，在某些情况下，Diels-Alder反应可以扩大使用复分解级联反应制备的分子支架的范围。

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