Readily available dicyclopentadiene derivatives were subjected to ring‐rearrangement metathesis in the presence of ruthenium catalysts to deliver a range of fused polycycle frameworks containing carbocycles, oxacycles, and azacycles. We have used atom‐economic processes such as ring‐rearrangement metathesis, Fischer indole cyclization, and the Diels–Alder reaction as key steps.

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A variety of structurally intricate polycycles have been assembled through ruthenium‐catalysed ring‐rearrangement metathesis of norbornene derivatives. The various substrates required for this work were prepared using Diels–Alder reactions and Grignard additions as key steps. Enyne ring‐rearrangement metathesis of a norbornene system containing a propargyl moiety produced a 1,3‐diene; this was then treated with an appropriate dienophile to deliver the corresponding cycloaddition product.

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SummaryA tricyclic lactam is reported in a four step synthesis sequence via Beckmann rearrangement and ring-rearrangement metathesis as key steps. Here, we used a simple starting material such as dicyclopentadiene.