title: Synthesis of LoganVir, a new carbocyclic nucleoside analogue.
abstract: Starting from a natural cyclopentanoid monoterpene belonging to the class of iridoid glucosides called loganin, we performed the synthesis of a new carbocyclic nucleoside, allowing the preparation of a new lead compound, with a potential HIV antiviral activity as an reverse transcriptase competitive inhibitor that we named LoganVir. The stereocontrol of the coupling reaction was completed utilizing the procedure described by Mitsunobu with a purinic base.
authors.affiliation: a Dipartimento di Chimica , Università di Roma "La Sapienza" , Roma , Italy.|b Consorzio CoSMeSe, Dipartimento di Scienze della Vita e dell'Ambiente , Università di Cagliari , Cagliari , Italy.
authors.forename: Luigi
authors.initials: L
authors.lastname: Ornano
authors.affiliation: a Dipartimento di Chimica , Università di Roma "La Sapienza" , Roma , Italy.|b Consorzio CoSMeSe, Dipartimento di Scienze della Vita e dell'Ambiente , Università di Cagliari , Cagliari , Italy.
authors.forename: Armandodoriano
authors.initials: A
authors.lastname: Bianco
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D060326:Chemistry Techniques, Synthetic; D003517:Cyclopentanes / Q000138:chemical synthesis*; D039823:Iridoids / Q000737:chemistry; D009705:Nucleosides / Q000737:chemistry / Q000494:pharmacology; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D031053:Vinca / Q000737:chemistry
chemical_list: D019380:Anti-HIV Agents; D003517:Cyclopentanes; D039823:Iridoids; C000619173:LoganVir; D009705:Nucleosides; D018894:Reverse Transcriptase Inhibitors; C059516:loganin; D000241:Adenosine
keywords: Antiviral agents; chiral intermediates; rearrangements; synthons; terpenoids