ConspectusSteroids continue to play a significant role in organic chemistry, medicinal chemistry, and drug discovery due to their important biological activities and diverse intriguing structures. Although synthetic organic chemists have successfully constructed and elaborated the classical [6-6-6-5] tetracyclic steroid skeleton for nearly a century, synthesis of the unusual rearranged steroids, particularly abeo-steroids with a medium-sized ring, remains a challenge in the synthetic community. Furthermore, the structures of abeo-steroids are complex and diverse, containing a seven-membered ring embedded in the fused or bridged A/B ring system and possessing numerous stereogenic centers. Besides their structural complexity, various abeo-steroids have shown remarkable biological activities. However, the relative scarcity of abeo-steroids in natural sources has impeded the systematic evaluation of their biological activities. In addition, direct strategies to build the core structures of abeo-steroids are very rare, partially because of the high ring-strain energies of their rearranged A/B ring systems. Therefore, the development of direct and efficient synthetic approaches to these complex molecules is highly desired.Our long-standing interest in the total synthesis of abeo-steroids and the development of new cycloaddition reactions for streamlining complex molecule synthesis have led us to develop a series of unique and powerful intramolecular cycloaddition strategies to access a diverse array of highly strained abeo-steroids. These strategies include Ru-catalyzed [5 + 2] cycloaddition, acid-promoted type I [5 + 2] cycloaddition, Rh-catalyzed [2 + 2 + 1] cycloaddition, and type II [5 + 2] cycloaddition. Since 2018, we have accomplished the first total syntheses of five synthetically challenging abeo-steroids, i.e., bufogargarizins A and B, phomarol, bufospirostenin A, and cyclocitrinol, thus facilitating the evaluation of their pharmacological potentials. In this Account, we summarize our laboratory's systematic efforts in the total synthesis of these abeo-steroids via cycloaddition strategies. We highlight the efficiency and versatility of each cycloaddition strategy for constructing structurally complex abeo-steroid cores by forming the A/B ring system. The evolution of each strategy and key lessons learned from the synthetic journey are also discussed. We believe that our unique perspective in this field will promote advances in the total synthesis of abeo- and related steroids.