Synthesis of Piperidine Nucleosides as Conformationally Restricted Immucillin Mimics.

Maria De Fenza, Anna Esposito, Daniele D'Alonzo, Annalisa Guaragna

Molecules (Basel, Switzerland) 2021 Mar 16

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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.

Citation

Maria De Fenza, Anna Esposito, Daniele D'Alonzo, Annalisa Guaragna. Synthesis of Piperidine Nucleosides as Conformationally Restricted Immucillin Mimics. Molecules (Basel, Switzerland). 2021 Mar 16;26(6)