New synthesis of (S)-dimethyl-4,4'-dimethoxy-5,6,5',6'-dimethenedioxy-biphenyl-2,2'-dicarboxylate by configuration transform

Bioorg Med Chem Lett. 2004 Apr 5;14(7):1665-7. doi: 10.1016/j.bmcl.2004.01.054.

Abstract

(R/S)-4,4'-Dimethoxy-5,6,5',6'-dimethenedioxy-2,2'-di-(4(S)-methyl-oxazoline-1)-biphenyl has been synthesized from dimethyl-4,4'-dimethoxy-5,6,5',6'-dimethenedioxy-biphenyl-2,2'-dicarboxylate, and then the diastereoisomer mixture was almost fully converted to a single diastereoisomer with S-configuration ((S)-3) through the key configuration transform promoted by CuI, which was confirmed by CD, HPLC and (13)C NMR. The C(2)-symmetric biphenyl, (S)-dimethyl-4,4'-dimethoxy-5,6,5',6'-dimethenedioxy-biphenyl-2,2'-dicarboxylate was prepared easily via the hydrolysis and ester exchange of (S)-3.

MeSH terms

  • Biphenyl Compounds / chemical synthesis*
  • Biphenyl Compounds / chemistry
  • Cyclooctanes / chemical synthesis
  • Cyclooctanes / chemistry
  • Dicarboxylic Acids / chemical synthesis*
  • Dicarboxylic Acids / chemistry
  • Lignans / chemical synthesis
  • Lignans / chemistry
  • Molecular Conformation
  • Polycyclic Compounds / chemical synthesis
  • Polycyclic Compounds / chemistry
  • Stereoisomerism

Substances

  • Biphenyl Compounds
  • Cyclooctanes
  • Dicarboxylic Acids
  • Lignans
  • Polycyclic Compounds
  • dimethoxy biphenyl monocarboxylate
  • schizandrin C