Cycloaddition reactions of carbohydrate derivatives. Part V. A hetero Diels-Alder approach to swainsonine analogs

Pál Herczegh, Imre Kovács, László Szilágyi, Ferenc Sztaricskai, Amaya Berecibar, Claude Riche, Angèle Chiaroni, Alain Olesker, Gabor Lukacs

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Diastereoselective hetero Diels-Alder reactions of sugar derived azomethines 4a-4g have been used for the construction of chiral piperidones 6 and 7. Configuration of the major products was 6,1′-threo in every case. The enone system of 6 and 7 was reduced diastereoselectively and subsequently swainsonine-analog hydroxyindolizidines 28-32 were prepared by an intramolecular reductive amination.

Original languageEnglish
Pages (from-to)13671-13686
Number of pages16
JournalTetrahedron
Volume50
Issue number48
DOIs
Publication statusPublished - 1994

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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