Chiral 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 het...Chiral 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(lil)-catalyzed asymmetric inverse-electron-demand Diels-Alder reactions of 2-pyrones.These reactions occur with vari-ous readily available dihydropyrroles and dihydrofurans as dienophiles,providing a step-economical synthetic platform for densely functionalized ciss-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.展开更多
基金the National Natural Science Foundation of China(Grant No.22071030)Fudan University for financial support。
文摘Chiral 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(lil)-catalyzed asymmetric inverse-electron-demand Diels-Alder reactions of 2-pyrones.These reactions occur with vari-ous readily available dihydropyrroles and dihydrofurans as dienophiles,providing a step-economical synthetic platform for densely functionalized ciss-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.
