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Adv."],"published-print":{"date-parts":[[2026,6,26]]},"abstract":"<jats:p>\n                    Constructing three-dimensional polycyclic scaffolds from a single precursor is a long-standing challenge in organic synthesis. Inspired by our proposed biosynthetic pathway of marine natural product ocellatusone C (\n                    <jats:bold>1<\/jats:bold>\n                    ), we achieved its concise biomimetic synthesis from tridachiahydropyrone (\n                    <jats:bold>2<\/jats:bold>\n                    ) through an acid-triggered cascade featuring a Dieckmann-type cyclization. This transformation further established a platform for skeletal diversification, yielding a series of [3.3.1] bicyclic analogs with broad functional tolerance. Guided by density functional theory (DFT) calculations, we uncovered a light-induced skeletal reorganization that efficiently generates elusive polycyclic architectures. Mechanistic investigations integrating DFT calculations and quasi-classical dynamics simulations revealed that selectivity in a critical vinylcyclopropane-cyclopentene rearrangement arises from post-spin crossing dynamic effects. Cross-coupling further expanded these scaffolds into a focused library of complex molecules. 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