Solid-phase Zincke route to pyridinium, tetrahydropyridine, and piperidine derivatives: Vesamicol analogs

Abstract Optically active derivatives of vesamicol are prepared using solid-phase chemistry. Zincke coupling of resin-bound amino ethers (trityl linker) with 2,4-dinitrophenyl pyridinium salts delivers Zincke products which can be (1) liberated from the resin (TFA) or (2) reduced (NaBH 4 ) to tetrahydropyridine derivatives and liberated. Subsequent reduction (H 2 /Pd) gives piperidines.