CYCLOADDITION REACTIONS OF CARBOHYDRATE-DERIVATIVES .5. A HETERO-DIELS-ALDER APPROACH TO SWAINSONINE ANALOGS

Authors
HERCZEGH P KOVACS I SZILAGYI L SZTARICSKAI F
Citation
P. Herczegh et al., CYCLOADDITION REACTIONS OF CARBOHYDRATE-DERIVATIVES .5. A HETERO-DIELS-ALDER APPROACH TO SWAINSONINE ANALOGS, Tetrahedron, 50(48), 1994, pp. 13671-13686
Citations number
53
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
48
Year of publication
1994
Pages
13671 - 13686
Database
ISI
SICI code
0040-4020(1994)50:48<13671:CROC.A>2.0.ZU;2-I
Abstract
Diastereoselective hetero Diels-Alder reactions of sugar derived azome thines 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 prepa red by an intramolecular reductive amination.