The domino reaction builds five stereocenters and iodinated polycycles, suggesting new synthetic routes for complex compounds.
We report a domino dearomative iodocyclization/intramolecular Diels-Alder (IMDA) reaction sequence that converts planar aromatic precursors into complex three-dimensional polycyclic scaffolds. The initial dearomative iodocyclization affords spirodienones, which can serve as dienophiles for a subsequent IMDA reaction with an internal diene. This protocol simultaneously creates three C-C bonds, three rings, and five stereocenters in a single step with excellent diastereoselectivity. This protocol is applicable to a broad range of substituents and ring systems for achieving iodinated, sp³-rich polycycles.
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Okitsu et al. (2025) studied this question.
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