Novel synthesis of optically active bishomotyrosine derivatives using the Friedel-Crafts reaction in triflic acid

Biosci Biotechnol Biochem. 2011;75(2):352-4. doi: 10.1271/bbb.100595. Epub 2011 Feb 7.

Abstract

We report here a novel synthesis of optically active bishomotyrosine. The bishomotyrosine skeleton was constructed by using a Friedel-Crafts reaction between phenol and optically active N-Tfa-Glu(Cl)-OMe in triflic acid under the mild condition. Reduction and subsequent deprotection then afforded bishomotyrosine derivatives without any loss of optical purity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Mesylates / chemistry*
  • Optical Phenomena*
  • Pentanoic Acids / chemistry
  • Stereoisomerism
  • Tyrosine / analogs & derivatives*
  • Tyrosine / chemical synthesis*

Substances

  • Mesylates
  • Pentanoic Acids
  • Tyrosine
  • trifluoromethanesulfonic acid