This review highlights recent advancements in the dearomatization strategy, a powerful approach for the total synthesis of complex natural products. Dearomatization involves converting planar, aromatic scaffolds into three-dimensional molecular architectures, facilitating the formation of carbon–carbon and carbon–heteroatom bonds, spontaneous cycloadditions, and cascade reactions. The review covers various strategies for dearomatization, including enzymatic and microbiological methods, carbene-based methodologies, oxidative dearomatization, and alkylative dearomatization. It also discusses the dearomatization of arenes, phenols, and heteroarenes, and their applications in the synthesis of complex natural products. Key examples include the synthesis of cedrene, (+)-cepharamine, (+)-trichodimerol, and (+)-bisorbicillinol. The review further explores the dearomatization of electron-rich heteroarenes such as furans, pyrroles, benzofurans, and indoles, and their use in the construction of complex chiral frameworks. Notable examples include the synthesis of stenine, (±)-merilactone A, and (±)-guanacastepene. The review emphasizes the importance of dearomatization in the total synthesis of complex natural products and its potential for future developments, including enantioselective dearomatization processes.This review highlights recent advancements in the dearomatization strategy, a powerful approach for the total synthesis of complex natural products. Dearomatization involves converting planar, aromatic scaffolds into three-dimensional molecular architectures, facilitating the formation of carbon–carbon and carbon–heteroatom bonds, spontaneous cycloadditions, and cascade reactions. The review covers various strategies for dearomatization, including enzymatic and microbiological methods, carbene-based methodologies, oxidative dearomatization, and alkylative dearomatization. It also discusses the dearomatization of arenes, phenols, and heteroarenes, and their applications in the synthesis of complex natural products. Key examples include the synthesis of cedrene, (+)-cepharamine, (+)-trichodimerol, and (+)-bisorbicillinol. The review further explores the dearomatization of electron-rich heteroarenes such as furans, pyrroles, benzofurans, and indoles, and their use in the construction of complex chiral frameworks. Notable examples include the synthesis of stenine, (±)-merilactone A, and (±)-guanacastepene. The review emphasizes the importance of dearomatization in the total synthesis of complex natural products and its potential for future developments, including enantioselective dearomatization processes.