An efficient enantioselective synthesis of (S)-(-)-acromelobic acid

Org Lett. 2000 Nov 2;2(22):3421-3. doi: 10.1021/ol006363l.

Abstract

[reaction: see text] A highly efficient enantioselective synthesis of (S)-(-)-acromelobic acid (1) was achieved via asymmetric hydrogenation of dehydroamino acid derivative (3) using (R,R)-[Rh(DIPAMP)(COD)]BF(4) catalyst followed by removal of protective groups in >98% ee and good over all yield. The key intermediate (3) was prepared from the commercially available citrazinic acid (4) in six steps.

MeSH terms

  • Alanine / analogs & derivatives*
  • Alanine / chemistry
  • Basidiomycota*
  • Catalysis
  • Indicators and Reagents
  • Molecular Structure
  • Pyridines / chemistry*
  • Stereoisomerism

Substances

  • Indicators and Reagents
  • Pyridines
  • acromelobic acid
  • Alanine