The diastereoselective asymmetric total synthesis of NG-391, a neuronal cell-protecting molecule

Yujiro Hayashi, Junichiro Yamaguchi, Mitsuru Shoji

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The stereocontrolled total synthesis of (+)-NG-391, a neuronal cell-protecting molecule, is described along with the determination of its absolute stereochemistry. The following reactions in this synthesis are particularly noteworthy: (1) The stereoselective construction of the conjugated (E,E,E,E,E)-pentaene from an (E,E,E)-alcohol using an IBX oxidation followed by stereoselective Horner-Emmons reaction. (2) The (E)-selective Knoevenagel condensation of a β-ketonitrile with a chiral 2-alkoxyaldehyde prepared from (S)-malic acid. (3) A diastereoselective epoxidation.

Original languageEnglish
Pages (from-to)9839-9846
Number of pages8
Issue number49
Publication statusPublished - 2002 Dec 2



  • IBX oxidation
  • Knoevenagel reaction
  • NG-391
  • Natural product

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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