Synthesis of guanine a-carboxy nucleoside phosphonate (G-a-CNP), a direct inhibitor of multiple viral DNA polymerases

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Synthesis of guanine a-carboxy nucleoside phosphonate (G-a-CNP), a direct inhibitor of multiple viral DNA polymerases

Maguire, Nuala M.; Ford, Alan; Balzarini, Jan; Maguire, Anita R.
Date: 2018-08-07
Copyright: © American Chemical Society. This document is the Accepted Manuscript version of a Published Work that will appear in final form in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/abs/10.1021/acs.joc.8b01124
Related: https://pubs.acs.org/doi/abs/10.1021/acs.joc.8b01124
Full text restriction information: Access to this article is restricted until 12 months after publication by request of the publisher.
Restriction lift date: 2019-08-07
Citation: Maguire, N. M., Ford, A., Balzarini, J. and Maguire, A. R. (2018) 'Synthesis of Guanine α-Carboxy Nucleoside Phosphonate (G-α-CNP), a direct inhibitor of multiple viral DNA polymerases', The Journal of Organic Chemistry, In Press, doi:10.1021/acs.joc.8b01124
Published Version: 10.1021/acs.joc.8b01124

Abstract:

The synthesis of guanine α-carboxy nucleoside phosphonate (G-α-CNP) is described. Two routes provide access to racemic G-α-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-α-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.

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