Concise synthesis of the anti-HIV nucleoside EFdA

Masayuki Kageyama, Takuho Miyagi, Mayumi Yoshida, Tomohiro Nagasawa, Hiroshi Ohrui, Shigefumi Kuwahara

    Research output: Contribution to journalArticlepeer-review

    13 Citations (Scopus)

    Abstract

    EFdA (4'-ethynyl-2-fluoro-2'-deoxyadenosine), a nucleoside reverse transcriptase inhibitor with extremely potent anti-HIV activity, was concisely synthesized from (R)-glyceraldehyde acetonide in an 18% overall yield by a 12-step sequence involving highly diastereoselective ethynylation of an α-alkoxy ketone intermediate. The present synthesis is superior, both in overall yield and in the number of steps, to the previous one which required 18 steps from an expensive starting material and resulted in a modest overall yield of 2.5%.

    Original languageEnglish
    Pages (from-to)1219-1225
    Number of pages7
    JournalBioscience, Biotechnology and Biochemistry
    Volume76
    Issue number6
    DOIs
    Publication statusPublished - 2012

    Keywords

    • AIDS
    • Anti-HIV
    • EFdA
    • N-glycosidation
    • Nucleoside

    ASJC Scopus subject areas

    • Biotechnology
    • Analytical Chemistry
    • Biochemistry
    • Applied Microbiology and Biotechnology
    • Molecular Biology
    • Organic Chemistry

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