Maguire, Nuala M.,Ford, Alan,Balzarini, Jan,Maguire, Anita R.

2018

Unknown

The Journal of Organic Chemistry

Synthesis of Guanine a-Carboxy Nucleoside Phosphonate (G-a-CNP), a direct inhibitor of multiple viral DNA polymerases

In Press

WOS: 6 ()

The synthesis of guanine a-carboxy nucleoside phosphonate (G-a-CNP) is described. Two routes provide access to racemic G-a-CNP 9, one via base construction and the other utilizing Tsuji–Trost allylic substitution. The latter methodology was also applied to the enantiopure synthesis of both antipodes of G-a-CNP, each of which shows interesting antiviral DNA polymerase activity. Additionally, we report an improved multi-gram scale preparation of the cyclopentene building block 10, starting material for the preferred Tsuji–Trost route to 9.

0022-3263

https://pubs.acs.org/doi/abs/10.1021/acs.joc.8b01124

10.1021/acs.joc.8b01124

Science Foundation Ireland

05/PICA/B802 and 14/TIDA/2402