Synthesis of the 5′-Fluoro-2′β-methyl analogues of neplanocin

Hiroki Kumamoto, Marina Kobayashi, Nobuyuki Kato, Jan Balzarini, Hiromichi Tanaka

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9 Citations (Scopus)

Abstract

Synthesis of the 5′-fluoro-2′-β-methyl analogues of neplanocin was carried out. Key intermediate cyclopentenone 19 was prepared from methyl α-D-mannopyranoside by a new approach consisting of ring-closing metathesis, stereoselective introduction of the 2′-methyl group, and intramolecular oxyselenenylation of the double bond as representative steps. Subsequent introduction of a fluorine atom at the 5′-position of 19 was performed by electrophilic fluorination by using Selectfluor Synthesis of 5′-fluoro-2′β-methyl analogues of neplanocin is described. The common carbocyclic unit was prepared from methyl α-D-mannopyranoside by ring-closing metathesis, stereoselective introduction of a methyl group, intramolecular oxyselenation, and electrophilic fluorination as representative steps.

Original languageEnglish
Pages (from-to)2685-2691
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number14
DOIs
Publication statusPublished - May 2011

Keywords

  • Carbocycles
  • Electrophilic addition
  • Fluorine
  • Nucleosides
  • Selenium

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Kumamoto, H., Kobayashi, M., Kato, N., Balzarini, J., & Tanaka, H. (2011). Synthesis of the 5′-Fluoro-2′β-methyl analogues of neplanocin. European Journal of Organic Chemistry, (14), 2685-2691. https://doi.org/10.1002/ejoc.201100062