Synthesis of hydroxylated bicyclic amino acids from L-tyrosine: octahydro-1H-indole carboxylates

J Org Chem. 2008 Oct 3;73(19):7807-10. doi: 10.1021/jo801552j. Epub 2008 Sep 4.

Abstract

A stereoselective approach to polyhydroxylated L-Choi derivatives has been developed. The oxidative cyclization of L-tyrosine was optimized to avoid partial racemization and to allow a more efficient scale-up.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Bridged Bicyclo Compounds / chemical synthesis*
  • Carboxylic Acids / chemistry
  • Hydroxylation
  • Indoles / chemistry
  • Stereoisomerism
  • Tyrosine / chemistry

Substances

  • Amino Acids
  • Bridged Bicyclo Compounds
  • Carboxylic Acids
  • Indoles
  • Tyrosine