Synthesis of Chain-Extended and C-6’ Functionalized Precursors of the Nucleoside Antibiotic Sinefungin

Academic Article

Abstract

  • Precursors of sinefungin were prepared by chain extension of the blocked adenosine 5′-aldehyde 4 through a carbon-carbon bond to C-5’. Bond formation was accomplished with variously functionalized stabilized ylides. Employment of 2-oxo-3-(triphenylphosphoranylidene)tetrahydrofuran (7) gave a nucleoside lactone (8) which was converted in several steps to a C-6’ carboxylic acid (10c). A Curtius rearrangement of this acid, quenching with benzyl alcohol, allowed the introduction of a C-6’ amino group, blocked as a urethane (11a). The chain-ending (C-8’) alcohol was converted to a leaving group and displaced by azide ion and dibenzyl sodiomalonate. © 1983, American Chemical Society. All rights reserved.
  • Published In

    Digital Object Identifier (doi)

    Pubmed Id

  • 11230987
  • Author List

  • Lyga JW; Secrist JA
  • Start Page

  • 1982
  • End Page

  • 1988
  • Volume

  • 48
  • Issue

  • 12