The first synthesis of 1'-fluoronucleosides.
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.
Kodama
Tetsuya
T
Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.
Matsuda
Akira
A
Shuto
Satoshi
S
D000963:Antimetabolites / Q000138:chemical synthesis* / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry*; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D000963:Antimetabolites; D005461:Fluorine; D014529:Uridine