Abstract
Comprehensive SummaryChiral heteroatom‐containing bicyclic scaffolds are important pharmacophores and prevalent in bioactive natural products and drug molecules. Herein, we report a unified approach for the divergent synthesis of chiral heteroatom‐containing bicyclic derivatives by lanthanide (III)‐catalyzed asymmetric inverse‐electron‐demand Diels–Alder reactions of 2‐pyrones. These reactions occur with various readily available dihydropyrroles and dihydrofurans as dienophiles, providing a step‐economical synthetic platform for densely functionalized cis‐hydroindoles and cis‐hydrobenzofurans with excellent yields and enantioselectivities. The synthetic utility of this approach is demonstrated by the concise synthesis of (–)‐α‐lycorane and (–)‐lycorine alkaloids.
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