Synthesis of D- and L-apio nucleoside analogues with 2′-hydroxyl group as potential anti-HIV agents

Dong Zhe Jin, Sung Hee Kwon, Hyung Ryong Moon, Prashantha Gunaga, Hea Ok Kim, Dae Kee Kim, Moon Woo Chun, Lak Shin Jeong

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

The present work describes the asymmetric synthesis of D- and L-apio-2′,3′-dideoxynucleoside analogues, 4 and 5 with 2′-hydroxyl group via a common intermediate 9, starting from D-galactose. Stereoselective dihydroxylation and deoxygenation through radical inversion were successfully employed to synthesize the key intermediate 12 with D-apio structure, while stereoselecetive hydroboration-oxidation was used for the synthesis of another key intermediate 18 with L-apio structure.

Original languageEnglish
Pages (from-to)1101-1109
Number of pages9
JournalBioorganic and Medicinal Chemistry
Volume12
Issue number5
DOIs
StatePublished - 1 Mar 2004

Keywords

  • Antiviral
  • Apio nucleotides
  • Stereoselective

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