Three-component reaction of sugar hydroxylactone, amine and isocyanide for the synthesis of iminosugars

The Ugi four-centre three-component strategy has been developed for the synthesis of iminosugars in good yields under catalyst-free conditions. This method proceeds through a bicyclic N-acyl-iminium intermediate followed by the attack of isonitrile resulting in the formation of dihydroxypyroglutamic...

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Bibliographic Details
Published in:Tetrahedron 2022-10, Vol.125, p.133021, Article 133021
Main Authors: Somnath, Bantu, Rajashaker, Nanubolu, Jagadeesh Babu, Reddy, G. Jithender, Reddy, B.V. Subba
Format: Article
Language:English
Subjects:
Amines
Hydroxylactone
Iminosugars
Isonitriles
Ugi reaction
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Summary:The Ugi four-centre three-component strategy has been developed for the synthesis of iminosugars in good yields under catalyst-free conditions. This method proceeds through a bicyclic N-acyl-iminium intermediate followed by the attack of isonitrile resulting in the formation of dihydroxypyroglutamic acid, which is a core moiety of many biologically important natural products. [Display omitted] •First report on synthesis of iminosugars from hydroxylactone.•Catalyst-free synthesis.•Ugi-four center three component reaction.•Alternate route for iminosugars.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2022.133021