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Diversity-oriented syntheses of 7-substituted lentiginosines |
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| Authors: | Franca M Cordero Paola BonannoMatteo Chioccioli Paola Gratteri Inmaculada RobinaAntonio J Moreno Vargas Alberto Brandi |
| Institution: | a Department of Chemistry ‘Ugo Schiff’ and HeteroBioLab, University of Firenze, via della Lastruccia 13, I-50019 Sesto Fiorentino (FI), Italy b Department of Pharmaceutical Sciences, Laboratory of Molecular Modeling Cheminformatics & QSAR and HeteroBioLab, University of Firenze, via U. Schiff 6, I-50019 Sesto Fiorentino (FI), Italy c Department of Organic Chemistry, University of Seville, Prof. García González, 1, E-41012-Seville, Spain |
| Abstract: | 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. |
| Keywords: | 1 3-Dipolar cycloaddition Iminosugar Indolizidine Glycosidase Triazole |
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