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ChemInform Abstract: Model Studies Towards the Synthesis of 4′-Azaerythrofuranosyladenines as Analogues of the Antiviral Drug 2′,3′-Dideoxyadenosine (ddA).

✍ Scribed by A. LEGGIO; A. LIGUORI; L. MAIUOLO; A. NAPOLI; A. PROCOPIO; C. SICILIANO; G. SINDONA

Publisher: John Wiley and Sons
Year: 2010
Weight: 33 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199810240

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✦ Synopsis

Model

Studies Towards the Synthesis of 4'-Azaerythrofuranosyladenines as Analogues of the Antiviral Drug 2',3'-Dideoxyadenosine (ddA).

-[3 + 2] Dipolar cycloaddition of nitrones to N-9-vinyladenine derivatives provides a regio-and stereoselective method for the synthesis of 4'-aza analogues of 2',3'-dideoxyadenosine, which may act as antiviral agents. The enantiopure sample (IX) is obtained by enzyme-catalyzed hydrolysis of an ester function introduced into the isoxazolidine nucleus.

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