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Diels-Alder 和 Stille 偶联方法在短保护基自由合成麦考酚酸及其苯亚磺酰基和苯硒基类似物中的应用,以及在水中的活性氧(ROS)探测能力。

Diels-Alder and Stille Coupling Approach for the Short Protecting-Group-Free Synthesis of Mycophenolic Acid, Its Phenylsulfenyl and Phenylselenyl Analogues, and Reactive Oxygen Species (ROS) Probing Capacity in Water.

机构信息

Department of Chemistry, Molecular Logic Gate Laboratory , Korea Advanced Institute of Science and Technology (KAIST) , Daejeon , 305-701 , Republic of Korea.

Center for Catalytic Hydrocarbon Functionalization , Institute for Basic Science (IBS) , Daejeon , 305-701 , Republic of Korea.

出版信息

Org Lett. 2018 Jun 15;20(12):3557-3561. doi: 10.1021/acs.orglett.8b01327. Epub 2018 May 29.

Abstract

A short, protecting-group-free synthesis is achieved. The synthesis is step-efficient and general. A Diels-Alder and Stille cross-coupling approach includes key transformations, allowing for a competitive synthesis which involves a rare halophenol Stille cross-coupling study. The phenylselenyl and phenylsulfenyl analogues were prepared as novel compounds in good overall yield. The applicability of one of the intermediates as a potential probe for reactive oxygen species (ROS) in water is investigated.

摘要

实现了一种简短的、无需保护基团的合成方法。该合成方法具有高效和通用性。通过 Diels-Alder 和 Stille 交叉偶联方法进行了关键转化,从而实现了具有竞争力的合成,其中包括对罕见的卤代苯酚 Stille 交叉偶联反应的研究。还以良好的总收率制备了苯硒基和苯亚磺酰基类似物作为新型化合物。研究了其中一种中间体作为水中活性氧(ROS)潜在探针的适用性。

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