Stereoselective synthesis of 3-hydroxymethyl-D-cyclopentenone, the versatile intermediate for the synthesis of carbocyclic nucleosides

Nucleosides Nucleotides Nucleic Acids. 2005;24(5-7):611-3. doi: 10.1081/NCN-200061832.

Abstract

The preparative and stereoselective synthesis (45- 50% overall yields, >50 g scale) of the key carbasugars 7a-d was achieved from D-ribose via stereoselective Grignard reaction and oxidative rearrangement as key reactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry
  • Catalysis
  • Cyclopentanes / chemical synthesis*
  • Cyclopentanes / chemistry*
  • Models, Chemical
  • Molecular Biology / methods*
  • Nucleosides / chemistry*
  • Oxygen / chemistry
  • Ribose / chemistry
  • Stereoisomerism

Substances

  • 3-hydroxymethylcyclopentenone
  • Alcohols
  • Cyclopentanes
  • Nucleosides
  • Ribose
  • cyclopentenone
  • Oxygen