化学
环异构化
吡咯烷
埃尼
分子内力
羟醛缩合
烯丙基重排
级联反应
催化作用
金属转移
组合化学
有机化学
立体化学
作者
Yujin Lee,Elise M. Rochette,Junyong Kim,David Y.‐K. Chen
标识
DOI:10.1002/ange.201705713
摘要
Abstract An asymmetric pathway to the caged tetracyclic pyrrolidine alkaloid, dendrobine, is reported. The successful synthetic strategy features a one‐pot, sequential palladium‐catalyzed enyne cycloisomerization and rhodium‐catalyzed diene‐assisted pyrrolidine formation by allylic CH activation. The developed transition‐metal‐catalyzed cascade process permits rapid access to the dendrobine core structure and circumvents the handling of labile intermediates. An intramolecular aldol condensation under carefully defined reaction conditions takes place with a concomitant detosylation, followed by reductive amine methylation, to afford a late‐stage intermediate (previously identified by several prior dendrobine syntheses) in only 10 synthetic steps overall.
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