A complementary strategy for the formal total synthesis of (±)-stelletins is reported. Key reactions include a diastereoselective Eschenmoser-Claisen rearrangement, a highly diastereoselective alkylation of decalin-nitrile, and an intramolecular [3 + 2] cycloaddition/N-O reductive bond cleavage to construct the strained functionalized tricyclic core of (±)-stelletins.
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