HOWELL RESEARCH GROUP

DEPARTMENT OF CHEMISTRY
UNIVERSITY OF CONNECTICUT

 

Synthesis of Nucleoside Analogues Using 1,5-Dioxaspiro[3.2]hexanes

Our interest in the nucleosides can be traced to three important observations:

1. The emergence or re-emergence of many viral and/or bacterial pathogens for which there are either no established treatment or which may have developed resistance to current therapies.


2. The successful inhibition of Human Simplex-Virus-2 (HSV-2) and HIV by the oxetane-containing natural product, oxetanocin A (12).


3. The observation that 2,2’-disubstituted nucleosides (psiconucleoside), i.e. those with a quaternary center adjacent to the base, bind to nucleic acids and show interesting biological activity.

Based on our ability to prepare 2,2’-disubstituted oxetanes (see 11), we are targeting novel nucleoside 13. These compounds will be assayed for potential antiviral, antibacterial or anticancer activity.

 

 

 

 

 

(1) Howell, A.R.; Ndakala, A.J. J. Org. Chem. 1998, 63, 6098-6099.
(2) Taboada, R; Ordonio, G. J. Org. Chem., 2003, 68, 1480-1488.