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Herein, we present a general photocatalytic skeletal editing strategy that enables a direct topological leap\u2014a single\u2010step reorganization that simultaneously alters both ring size and fusion topology\u2014from readily available five\u2010 to eight\u2010membered cyclic ketones into diverse seven\u2010 to ten\u2010membered cyclopropane\u2010fused medium rings. This transformation proceeds through a novel energy\u2010transfer\u2010induced, diradical\u2010mediated 1,4\u2010carbonyl migration, orchestrating a \u201cring expansion\u2013collapse\u201d cascade to forge the strained bicyclic frameworks straightforward, which is supported by DFT calculations. This strategy features broad substrate scope, excellent functional\u2010group compatibility, and high efficiency, enabling the late\u2010stage diversification of complex molecules and exploration of CFMR chemical space that was previously inaccessible. Moreover, integration of this strategy with further skeletal modification enables rapid construction of versatile [n.3.0] bicycles.<\/jats:p>","DOI":"10.1002\/anie.202522620","type":"journal-article","created":{"date-parts":[[2026,1,10]],"date-time":"2026-01-10T14:22:46Z","timestamp":1768054966000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Energy\u2010Transfer\u2010Enabled Skeletal Rearrangement of Cyclic Ketones into Strained Cyclopropane\u2010Fused Medium Rings"],"prefix":"10.1002","volume":"65","author":[{"given":"Yingru","family":"Xu","sequence":"first","affiliation":[{"name":"Hubei Key Laboratory of Bioinorganic Chemistry &amp; Medica Hubei Engineering Research Center for Biomaterials and Medical Protective Materials School of Chemistry and Chemical Engineering Huazhong University of Science and Technology (HUST)  1037 Luoyu Road Wuhan 430074 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