Convenient synthesis of epimeric indolizidines by the intramolecular 1,3-dipolar cycloaddition of a sugar derived N-(3-alkenyl)nitrone

The stereoselective synthesis of two epimeric penta-hydroxylated indolizidines was accomplished from 2,3:5,6-di-O-isopropylidene-α-d-mannofuranose and N-(2-methylpent-4-en-2-yl)hydroxylamine. The transformation of these substrates into the corresponding 7-oxa-1-azabicyclo[2.2.1]heptane by the intram...

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Bibliographic Details
Published in:Tetrahedron 2013-11, Vol.69 (46), p.9826-9831
Main Authors: Mironiuk-Puchalska, Ewa, Rowicki, Tomasz, Sas, Wojciech, Koszytkowska-Stawińska, Mariola
Format: Article
Language:English
Subjects:
Catalysis
Cycloaddition
Hydrogenation
Intramolecular 1,3-dipolar cycloaddition
Polyhydroxylated indolizidines
Sodium azides
Stereoselective reduction
Sugar nitrones
Sugars
Synthesis
Tetrahedrons
Transformations
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Summary:The stereoselective synthesis of two epimeric penta-hydroxylated indolizidines was accomplished from 2,3:5,6-di-O-isopropylidene-α-d-mannofuranose and N-(2-methylpent-4-en-2-yl)hydroxylamine. The transformation of these substrates into the corresponding 7-oxa-1-azabicyclo[2.2.1]heptane by the intramolecular 1,3-dipolar cycloaddition was the key step of the synthesis. The adduct was transformed into the tricyclic ammonium salt by intramolecular N-alkylation. The tricyclic ammonium salt was converted to the target compounds by: (route 1) the catalytic hydrogenation; or (route 2) the reaction with sodium azide, followed by the enantioselective reduction of the resulting indolizidinone. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.09.008