With the aim to expand the repertoire of these bioactive nucleosides, we are currently exploring the antiviral properties of novel cyclohexenyl nucleosides 2 and ent-2, lacking the OH group at C5' position and therefore being conceived as chain terminators. Herein, the asymmetric synthesis of 2 and ent-2 (B = Pu or Py) starting from achiral cyclohexanone is reported (Figure 2). Main attention has been devoted to the key Tsuji-Trost rearrangement step of 3 and ent-3, whose unprecedented stereoconvergent outcome has been studied by chemical methods, as well as, by spectroscopic and in silico analysis.
Asymmetric Synthesis and Antiviral Activity of Novel Carbocyclic Nucleosides
Esposito, Anna;De Fenza, Maria;Talarico, G.;Guaragna, A.;D’Alonzo, Daniele
2017
Abstract
With the aim to expand the repertoire of these bioactive nucleosides, we are currently exploring the antiviral properties of novel cyclohexenyl nucleosides 2 and ent-2, lacking the OH group at C5' position and therefore being conceived as chain terminators. Herein, the asymmetric synthesis of 2 and ent-2 (B = Pu or Py) starting from achiral cyclohexanone is reported (Figure 2). Main attention has been devoted to the key Tsuji-Trost rearrangement step of 3 and ent-3, whose unprecedented stereoconvergent outcome has been studied by chemical methods, as well as, by spectroscopic and in silico analysis.File in questo prodotto:
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