Diversity-oriented syntheses of 7-substituted lentiginosines

• Published in: Tetrahedron 2011-12, Vol.67 (49), p.9555-9564
• Main Authors: Cordero, Franca M., Bonanno, Paola, Chioccioli, Matteo, Gratteri, Paola, Robina, Inmaculada, Moreno Vargas, Antonio J., Brandi, Alberto
• Format: Article
• Language: English
• Subjects: 1,3-Dipolar cycloaddition; Alkynes; Amino acids; Assembling; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemistry; Cycloaddition; Derivatives; Exact sciences and technology; Glycosidase; 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; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Iminosugar; Indolizidine; Inhibitors; Modular; Organic chemistry; Preparations and properties; Tetrahedrons; Triazole
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2011.10.008

Diversity-oriented synthesis of derivatives of the potent glycosidase inhibitor lentiginosine can be achieved in an efficient and versatile way by two modular approaches on key intermediates. After assembling the indolizidine ring system through 1,3-dipolar cycloaddition of a dihydroxylated pyrroline N-oxide with 4-butenol followed by elaboration of the isoxazolidine moiety, the 7-amino and 7-azido derivatives synthesized can be conjugated with functionalised chains by coupling, respectively, with an amino acid, or an alkyne in copper-catalyzed Huisgen cycloadditions. [Display omitted]