Toward the Synthesis of Potential Antiviral Carbocyclic Nucleosides

Abstract: Human immunodeficiency virus, most commonly referred to as HIV, is a persistent problem in the United States. While therapies are becoming more widely available to prevent and treat symptoms of this virus, there is currently no cure for HIV.¹ One of the first steps taken to transform this otherwise fatal virus into a manageable ailment was the creation of nucleoside reverse transcriptase inhibitors. HAART, highly active antiretroviral therapy, utilizes nucleoside reverse transcriptase inhibitors as well as HIV-1 protease inhibitors in order to suppress the viral load of HIV-1.² The primary focus of this research is to synthesize a library of potential antiviral carbocyclic nucleosides that could further be tested for antiviral efficacy. Carbocyclic nucleosides are analogs of naturally occurring nucleosides where carbon replaces the endocyclic oxygen. Commonly referred to as carbanucleosides, these metabolically stable compounds could exhibit antibiotic as well as antiviral potency.³

References

1. Center for Disease Control and Prevention. https://www.cdc.gov/hiv/basics/statistics.html.
2. Gosh, A. K.; Osswald, H. L.; Prato, G., Recent Progress in the Development of HIV-1 Protease Inhibitors for the Treatment of HIV/AIDS. National Library of Medicine 2016, 59 (11), 5172-5208.
3. Li, F.; Brogan, B. J.; Gage, J. L.; Zhang, D.; Miller, M. J.; Chemoenzymatic Synthesis and Synthetic Application of Enantiopure Aminocyclopentenols: Total Synthesis of Carbocyclic (+)-Uracil Polyoxin C and Its α-Epimer. JOC 2004, 69 (4538-4540).