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Significance: Cage compounds, such as 6 and 7, are polycyclic molecules that often contain several conjoined strained ring systems. Accordingly, they can be synthetically challenging to access. This report offers an efficient and scalable route to several unique cage compounds that feature oxepane and tetrahydrofuran ring systems. Distinctively, compound 6 contains three-, four-, five-, six-, and seven-membered rings.

Comment: The central ring systems of 6 and 7 were synthesized from benzoquinone 1 beginning with a Diels–Alder cycloaddition and followed by a photochemical [2+ 2] cycloaddition (eg, 3 to 4). A key step was the twofold ring-closing metathesis of 5, which proceeded to form the peripheral ring systems shown with complete selectivity.