Inverse-Electron-Demand Diels–Alder Reactions of 2-Pyrones: Bridged Lactones and Beyond |
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| Authors: | Guanghao Huang Prof Cyrille Kouklovsky Dr Aurélien de la Torre |
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| Institution: | Université Paris-Saclay, CNRS, Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), 15, rue Georges Clémenceau, 91405 Orsay Cedex, France |
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| Abstract: | 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 CO2 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. |
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| Keywords: | 2-pyrone Diels–Alder reaction inverse-electron-demand synthetic methods total synthesis |
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