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微波辅助烯烃复分解反应作为生物活性化合物合成中的关键步骤。

Microwave-assisted Olefin Metathesis as Pivotal Step in the Synthesis of Bioactive Compounds.

作者信息

Etse Koffi Senam, Ngendera Alice, Ntumba Nelly Tshibalonza, Demonceau Albert, Delaude Lionel, Dragutan Ileana, Dragutan Valerian

机构信息

Laboratory of Macromolecular Chemistry and Organic Catalysis, Department of Chemistry, University of Liege, Sart-Tilman (B.6a), B-4000 Liege, Belgium.

Laboratory of Organometallic Chemistry and Homogeneous Catalysis, Department of Chemistry, University of Liege, Sart-Tilman (B.6a), B-4000 Liege, Belgium.

出版信息

Curr Med Chem. 2017;24(41):4538-4578. doi: 10.2174/0929867324666170314122820.

Abstract

Over the last two decades, olefin metathesis has emerged as a new avenue in the design of new routes for the synthesis of natural products and active pharmaceutical ingredients. In many cases, syntheses based on olefin metathesis strategies provide significant routes in terms of increasing the overall yields, improving the synthesis scope, and decreasing the number of steps. On the other hand, over the last decade, microwave-assisted chemistry has experienced an incredible development, which rapidly opened new areas in organic synthesis and in homogeneous catalysis. In this review article, we highlight applications of microwaveheated olefin metathesis reactions as pivotal steps in the total synthesis of biologically active compounds. By drawing selected examples from the recent literature, we aim to illustrate the great synthetic power and variety of metathesis reactions, as well as the beneficial effects of microwave irradiation over conventional heating sources. The majority of the selected applications of microwave-assisted olefin metathesis cover the synthesis of medium-ring cycles, macrocycles, and peptidomimetics by means of ring-closing metathesis (RCM) and crossmetathesis (CM) routes.

摘要

在过去二十年中,烯烃复分解反应已成为设计天然产物和活性药物成分合成新路线的一条新途径。在许多情况下,基于烯烃复分解策略的合成方法在提高总产率、拓展合成范围和减少反应步骤方面提供了重要途径。另一方面,在过去十年中,微波辅助化学取得了惊人的发展,迅速在有机合成和均相催化领域开辟了新的方向。在这篇综述文章中,我们重点介绍了微波加热烯烃复分解反应在生物活性化合物全合成中的关键步骤应用。通过从近期文献中选取实例,我们旨在说明复分解反应强大的合成能力和多样性,以及微波辐射相较于传统加热源的有益效果。微波辅助烯烃复分解反应的大多数选定应用涵盖了通过关环复分解(RCM)和交叉复分解(CM)路线合成中环、大环和拟肽。

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