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Synthesis of Piperidine Nucleosides as Conformationally Restricted Immucillin Mimics |
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| Authors: | Maria De Fenza Anna Esposito Daniele D&#x;Alonzo Annalisa Guaragna |
| Institution: | 1.Department of Chemical Sciences, University of Naples Federico II, Via Cintia, 80126 Naples, Italy; (M.D.F.); (A.E.); (D.D.);2.Department of Chemical, Materials and Production Engineering, University of Naples Federico II, Piazzale V. Tecchio 80, 80125 Naples, Italy |
| Abstract: | The de novo synthesis of piperidine nucleosides from our homologating agent 5,6-dihydro-1,4-dithiin is herein reported. The structure and conformation of nucleosides were conceived to faithfully resemble the well-known nucleoside drugs Immucillins H and A in their bioactive conformation. NMR analysis of the synthesized compounds confirmed that they adopt an iminosugar conformation bearing the nucleobases and the hydroxyl groups in the appropriate orientation. |
| Keywords: | immucillins nucleoside analogues de novo synthesis iminosugars biomimetics conformationally restricted nucleosides piperidine nucleosides polymer-supported triphenyl phosphine |