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- Title
An Asymmetric Pathway to Dendrobine by a Transition-Metal-Catalyzed Cascade Process.
- Authors
Lee, Yujin; Rochette, Elise M.; Kim, Junyong; Chen, David Y.‐K.
- 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.
- Subjects
CYCLOISOMERIZATION; METHYLATION; ORGANIC synthesis; OXIDATION-reduction reaction; ALKALOIDS
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 40, p12418
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201705713