3 years ago

An Asymmetric Pathway to Dendrobine by a Transition-Metal-Catalyzed Cascade Process

An Asymmetric Pathway to Dendrobine by a Transition-Metal-Catalyzed Cascade Process
Yujin Lee, David Y.-K. Chen, Elise M. Rochette, Junyong Kim
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. An asymmetric pathway to polycyclic alkaloid dendrobine was developed comprising a one-pot palladium-catalyzed enyne cycloisomerization, and rhodium-catalyzed diene-assisted pyrrolidine formation by allylic CH activation. Intramolecular aldol condensation with concomitant detosylation, followed by reductive amination, afforded an advanced intermediate in only 10 synthetic steps.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201705713

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