Novel synthesis of L-ribose from D-mannono-1,4-lactone

Org Lett. 2002 Jul 11;4(14):2401-3. doi: 10.1021/ol026141i.

Abstract

[reaction: see text] D-Mannono-1,4-lactone was efficiently converted into L-ribose in eight steps. A key step of this synthesis is the cyclization of a gamma-hydroxyalkoxamate under Mitsunobu conditions. It is noteworthy that the O-alkylation product was obtained in 94% yield and that none of the N-alkylation product was detected in this cyclization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemistry*
  • Alkylation
  • Cyclization
  • Indicators and Reagents
  • Ribose / chemical synthesis*

Substances

  • Indicators and Reagents
  • mannono-1,4-lactone
  • Ribose
  • 4-Butyrolactone