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Four C-C bonds, four rings, and eight contiguous stereocenters in one go! Tetracyclic product 2, which results on warming simple acyclic precursor 1 with a mild Lewis acid, is formed through an efficient and highly stereoselective domino sequence of two intramolecular Diels-Alder reactions. Pharmacologically important norsteroids are just one potential application of this extremely effective approach to fused polycyclic systems.
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Nörret et al. (2001) studied this question.
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