Stereoselective synthesis by double reductive amination ring closure of novel aza-heteroannulated sugars

• Published in: Tetrahedron Vol. 65; no. 24; pp. 4766 - 4774
• Main Authors: Laventine, Dominic M., Davies, Michelle, Evinson, Emma L., Jenkins, Paul R., Cullis, Paul M., García, Marcos D.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 13.06.2009; Elsevier
• Subjects: Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; GLYCOSIDASE INHIBITORY-ACTIVITY; ROUTE; NATURAL OCCURRENCE; ANALOGS; ALKALOIDS; Ozonolysis; Enzyme; Nitrogen heterocycle; Enzyme inhibitor; Oside; Selectivity; Diketone; Tandem reaction; Diastereoselectivity; Pyrrolidine derivatives; Glycosylases; Chemical reduction; Stereoselectivity; Alkene; Amination; Cyclization; Wacker Oxidation; Glycosidases; Hydrolases; Glycoside; Inhibition; Chemical synthesis; Ethylenic compound; β-Galactosidase
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2009.04.011

We present here the stereoselective synthesis of a series of 2/3- N-pyrrolidine derivatives of glycosides produced by diastereoselective double reductive amination ring closure of 1,4-dicarbonyl compounds. These precursors were produced by tandem ozonolysis–reduction or Wacker oxidation of known alkenes. The potential of these new compounds as glycosidase inhibitors is illustrated for compound 16, showing selective inhibition of β- d-galactosidase. [Display omitted]