Asymmetric total syntheses of aspidodasycarpine, lonicerine, and the proposed structure of lanciferine
Aspidodasycarpine and lonicerine are a pair of epimeric aspidophylline-type alkaloids
bearing vicinal quaternary C7 and C16. The first and enantioselective total syntheses of
these molecules are described here. A Ru-catalyzed asymmetric transfer hydrogenation
established the first stereocenter. An Au-promoted Toste cyclization was exploited to
assemble the bridged tetracyclic core and define the geometry of the exocyclic olefin;
electron deficient (p-CF3C6H4) 3P was a suitable ligand for this transformation. An aldol …
bearing vicinal quaternary C7 and C16. The first and enantioselective total syntheses of
these molecules are described here. A Ru-catalyzed asymmetric transfer hydrogenation
established the first stereocenter. An Au-promoted Toste cyclization was exploited to
assemble the bridged tetracyclic core and define the geometry of the exocyclic olefin;
electron deficient (p-CF3C6H4) 3P was a suitable ligand for this transformation. An aldol …
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