Université Paris-Saclay, CNRS, Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), 15, rue Georges Clémenceau, 91405, Orsay Cedex, France.
Chemistry. 2021 Mar 12;27(15):4760-4788. doi: 10.1002/chem.202003980. Epub 2021 Jan 12.
Inverse-electron-demand Diels-Alder (IEDDA) reactions of electron-poor 2-pyrones as electrophilic dienes have been extensively studied in the past fifty years. These reactions provide an efficient access to bridged bicyclic lactones and their derivatives, such as densely functionalized 1,3-cyclohexadienes after CO extrusion and polysubstituted aromatic compounds through elimination. This reaction has been used for the synthesis of many biologically active natural products and drug candidates. In this review, the developments of these IEDDA reactions including non-catalytic, Lewis acid-catalyzed and organocatalytic IEDDA reactions, and their applications in total synthesis are discussed in detail.
过去五十年中，缺电子 2-吡喃酮作为亲双烯体的逆电子需求 Diels-Alder (IEDDA) 反应得到了广泛研究。这些反应为桥环双环内酯及其衍生物的合成提供了有效途径，如 CO 挤出后的稠合官能化 1,3-环己二烯和消除后的多取代芳族化合物。该反应已用于许多生物活性天然产物和药物候选物的合成。在本文综述中，详细讨论了包括非催化、路易斯酸催化和有机催化 IEDDA 反应在内的这些 IEDDA 反应的发展及其在全合成中的应用。
