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Abstract Asymmetric total synthesis of the hasubanan alkaloids periglaucines A–C, N,O-dimethyloxostephine and oxostephabenine is described. The key strategies include: 1) a RhI-catalyzed regio- and diastereoselective Hayashi-Miyaura reaction; 2) an intramolecular photoenolization/Diels–Alder (PEDA) reaction; and 3) bio-inspired intramolecular Michael addition and transannular acetalization.
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