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Updated: Feb 24, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
An Asymmetric Pathway to Dendrobine by a Transition-Metal-Catalyzed Cascade Process
Yujin Lee1, Elise M Rochette1, Junyong Kim1
1Department of Chemistry, Seoul National University, Gwanak-1 Gwanak-ro, Gwanak-gu, Seoul, 151-742, South Korea.
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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