Diastereoselective synthesis of a spironoraristeromycin using an acylnitroso Diels-Alder reaction

J Org Chem. 2009 Aug 21;74(16):5941-6. doi: 10.1021/jo900877b.

Abstract

The tert-butyl N-hydroxycarbamate-derived nitroso reagent 1 reacted with N-Cbz-protected spirocyclic diene 2 to provide spirocycloadduct 3. Here we describe the efficient conversion of 3 into the novel carbocyclic nucleoside spironoraristeromycin 4.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / chemical synthesis
  • Adenosine / chemistry
  • Models, Molecular
  • Molecular Conformation
  • Nitroso Compounds / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Nitroso Compounds
  • 5'-noraristeromycin
  • Adenosine