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Nucleic Acids Symposium Series 2006 50(1):3-4; doi:10.1093/nass/nrl002
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© 2006 Oxford University Press

The first synthesis of 1'-fluoronucleosides

Tetsuya Kodama, Akira Matsuda and Satoshi Shuto

Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan

The first synthesis of 1'-fluoronucleosides, which has long been synthetic targets as the potential antimetabolites, was achieved. Electrophilic fluorination of the 1'-position of a 1'-ketouridine derivative, followed by reduction of the 2'-keto-moiety, gave the protected 1'-fluorouridine derivative and its arabino-type congener. Alternatively, nucleophilic fluorination of a 1'-phenyselenouridine derivative with DAST/NBS produced the protected 1'-fluorouridine and its {alpha}-anomer.


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