Synthesis of a protected 3,4-dihydroxyproline from a pentose sugar

Org Lett. 1999 Sep 9;1(5):787-9. doi: 10.1021/ol990763v.

Abstract

[reaction: see text] D-Ribonolactone (6) was transformed into N-((fluorenylmethoxy)carbonyl)-3,4-bis-O-(tert-butyldimethylsilyl)-D-2,3-cis-3,4-cis-3,4-dihydroxyproline (13) in nine chemical steps. This represents a potentially general strategy for the synthesis of 3,4-dihydroxyprolines, utilizing the pentose sugar series as starting materials.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aluminum Compounds
  • Animals
  • Aza Compounds / chemistry
  • Hydroxyproline / chemical synthesis*
  • Indicators and Reagents
  • Lithium Compounds
  • Magnetic Resonance Spectroscopy
  • Pentoses / chemistry*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • 3,4-dihydroxyproline
  • Aluminum Compounds
  • Aza Compounds
  • Indicators and Reagents
  • Lithium Compounds
  • Pentoses
  • lithium aluminum hydride
  • Hydroxyproline