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 showing interesting antiviral DNA polymerase activity. Additionally, we report an improved multigram scale preparation of the cyclopentene building block 10, starting material for the preferred Tsuji-Trost route to 9.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Catalysis
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Chemistry Techniques, Synthetic
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DNA-Directed DNA Polymerase / metabolism*
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Guanine / chemistry*
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HIV-1 / enzymology
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Nucleic Acid Synthesis Inhibitors / chemical synthesis*
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Nucleic Acid Synthesis Inhibitors / chemistry
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Nucleic Acid Synthesis Inhibitors / pharmacology*
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Organophosphonates / chemical synthesis*
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Organophosphonates / chemistry
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Organophosphonates / pharmacology*
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Palladium / chemistry
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Purine Nucleosides / chemistry*
Substances
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Nucleic Acid Synthesis Inhibitors
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Organophosphonates
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Purine Nucleosides
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Palladium
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Guanine
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DNA-Directed DNA Polymerase