Abstract An enantioselective synthesis of (?)‐10‐hydroxyacutuminine is reported. Central to our strategy is a photochemical 2+2 cycloaddition that forges two of the quaternary stereocenters present in the acutumine alkaloids. A subsequent retro‐aldol/Dieckmann sequence furnishes the spirocyclic cyclopentenone. Efforts to chlorinate the acutumine scaffold at C10 under heterolytic or radical deoxychlorination conditions led to the synthesis of an unexpected cyclopropane‐containing pentacycle.
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