A remarkably simple chemicoenzymatic approach to structurally complex bicyclo[3.1.0]hexane carbocyclic nucleosides

Org Lett. 2000 Nov 30;2(24):3793-6. doi: 10.1021/ol000238s.

Abstract

[reaction: see text] Intramolecular cyclopropanation of a carbene engendered from the corresponding diazo beta-ketoester produced the desired bicyclo[3.1. 0]hexane pseudosugar. Purine nucleosides obtained via Mitsunobu coupling were resolved with adenosine deaminase. The requisite beta-ketoester was assembled in one step from ethyl acetoacetate and acrolein.

MeSH terms

  • Acetoacetates
  • Acrolein
  • Bridged Bicyclo Compounds / chemical synthesis*
  • Chromatography, High Pressure Liquid
  • Cyclization
  • Indicators and Reagents
  • Nucleosides / chemical synthesis*
  • Protein Conformation

Substances

  • Acetoacetates
  • Bridged Bicyclo Compounds
  • Indicators and Reagents
  • Nucleosides
  • Acrolein