基于微波的反应筛选：邻醌二聚体的串联反-Diels-Alder/Diels-Alder 环加成反应。
Microwave-based reaction screening: tandem retro-Diels-Alder/Diels-Alder cycloadditions of o-quinol dimers.
机构信息
Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, Boston, Massachusetts 02215, United States.
出版信息
J Org Chem. 2011 Nov 4;76(21):8944-54. doi: 10.1021/jo201658y. Epub 2011 Oct 7.
Abstract
We have accomplished a parallel screen of cycloaddition partners for o-quinols utilizing a plate-based microwave system. Microwave irradiation improves the efficiency of retro-Diels-Alder/Diels-Alder cascades of o-quinol dimers which generally proceed in a diastereoselective fashion. Computational studies indicate that asynchronous transition states are favored in Diels-Alder cycloadditions of o-quinols. Subsequent biological evaluation of a collection of cycloadducts has identified an inhibitor of activator protein-1 (AP-1), an oncogenic transcription factor.
摘要
我们利用基于平板的微波系统对邻醌二醇的环加成伙伴进行了平行筛选。微波辐射提高了邻醌二醇二聚体的反-Diels-Alder/Diels-Alder 级联反应的效率，该反应通常以立体选择性方式进行。计算研究表明，邻醌二醇的 Diels-Alder 环加成反应中有利于异步过渡态。随后对一系列环加成产物的生物学评估鉴定出了一种激活蛋白-1（AP-1）抑制剂，这是一种致癌转录因子。
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