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Synthesis 2006(18): 2993-2995  
DOI: 10.1055/s-2006-942544
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

A Novel Method for the Introduction of Fluorine into the Purine 2-Position: Synthesis of 2-Fluoroadenosine and a Formal Synthesis of the Antileukemic Drug Fludarabine

Morten Brændvang, Lise-Lotte Gundersen*
Department of Chemistry, University of Oslo, P.O. Box 1033, Blindern, 0315 Oslo, Norway
Fax: +47(22)855507; e-Mail: l.l.gundersen@kjemi.uio.no;
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Publikationsverlauf

Received 23 April 2006
Publikationsdatum:
02. August 2006 (online)

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Abstract

A novel method for the introduction of fluorine in the purine 2-position is described and employed in the synthesis of a potential antimycobacterial compound. Also 2-fluoroadenosine has been synthesized for the first time from adenosine with perbenzo­ylated 2-nitroadenosine as a key intermediate. Mild reaction conditions are employed and few synthetic steps are required. The novel synthesis of fluoroadenosine can be regarded as a formal synthesis of the antileukemic drug fludarabine phosphate.

Key words

anticancer agents - fluorination - nitration - nucleosides - purines

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