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

11 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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