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

Yujiro Hayashi, Junichiro Yamaguchi, Mitsuru Shoji

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

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
JournalTetrahedron
Volume58
Issue number49
DOIs
Publication statusPublished - 2002 Dec 2

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'The diastereoselective asymmetric total synthesis of NG-391, a neuronal cell-protecting molecule'. Together they form a unique fingerprint.

Cite this