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

P. Herczegh, Imre Kovács, László Szilágyi, F. 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

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Piperidones
Swainsonine
Amination
Cycloaddition
Cycloaddition Reaction
Sugars
Carbohydrates
Derivatives

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Cycloaddition reactions of carbohydrate derivatives. Part V. A hetero Diels-Alder approach to swainsonine analogs. / Herczegh, P.; Kovács, Imre; Szilágyi, László; Sztaricskai, F.; Berecibar, Amaya; Riche, Claude; Chiaroni, Angèle; Olesker, Alain; Lukacs, Gabor.

In: Tetrahedron, Vol. 50, No. 48, 1994, p. 13671-13686.

Research output: Contribution to journalArticle

Herczegh, P, Kovács, I, Szilágyi, L, Sztaricskai, F, Berecibar, A, Riche, C, Chiaroni, A, Olesker, A & Lukacs, G 1994, 'Cycloaddition reactions of carbohydrate derivatives. Part V. A hetero Diels-Alder approach to swainsonine analogs', Tetrahedron, vol. 50, no. 48, pp. 13671-13686. https://doi.org/10.1016/S0040-4020(01)85680-5
Herczegh, P. ; Kovács, Imre ; Szilágyi, László ; Sztaricskai, F. ; Berecibar, Amaya ; Riche, Claude ; Chiaroni, Angèle ; Olesker, Alain ; Lukacs, Gabor. / Cycloaddition reactions of carbohydrate derivatives. Part V. A hetero Diels-Alder approach to swainsonine analogs. In: Tetrahedron. 1994 ; Vol. 50, No. 48. pp. 13671-13686.
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