Synthesis of C-aryldeoxyribosides by [2 + 2 + 2]-cyclotrimerization catalyzed by Rh, Ni, Co, and Ru complexes

Org Lett. 2006 May 11;8(10):2051-4. doi: 10.1021/ol060454m.

Abstract

[reaction: see text] A novel approach to the synthesis of functionalized C-nucleosides was developed. Cyclotrimerization of C-alkynyldeoxyriboside with a variety of substituted 1,6-heptadiynes to the corresponding C-aryldeoxyribosides was catalyzed by various transition metal complexes (Rh, Ir, Co, Ru, and Ni). The most general catalyst proved to be RhCl(PPh(3))(3), which could catalyze most of the cyclotrimerizations in high yields (52-95%).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cobalt / chemistry
  • Cyclization
  • Deoxyribonucleosides / chemical synthesis*
  • Deoxyribonucleosides / chemistry
  • Molecular Structure
  • Nickel / chemistry
  • Rhodium / chemistry
  • Ruthenium / chemistry

Substances

  • Deoxyribonucleosides
  • Cobalt
  • Nickel
  • Ruthenium
  • Rhodium