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The first asymmetric total synthesis of (−)‐stemonamine is described. The key reactions included intramolecular acylation to construct the seven‐membered ring and a tandem [2+2] cycloaddition‐Dieckmann condensation reaction using an ynolate to form the fully substituted cyclopentenone moiety. Racemization and epimerization of the natural product were first experimentally demonstrated.
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