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

Masahiro Eda, Mark J. Kurth

Research output: Contribution to journalArticle

14 Scopus citations

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 (NaBH4) to tetrahydropyridine derivatives and liberated. Subsequent reduction (H2/Pd) gives piperidines.

Original languageEnglish (US)
Pages (from-to)2063-2068
Number of pages6
JournalTetrahedron Letters
Volume42
Issue number11
DOIs
StatePublished - Mar 11 2001

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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