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
Externally publishedYes

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Alkenes
Alcohols
Stereochemistry
Molecules
Epoxidation
Condensation
Oxidation
malic acid

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

The diastereoselective asymmetric total synthesis of NG-391, a neuronal cell-protecting molecule. / Hayashi, Yujiro; Yamaguchi, Junichiro; Shoji, Mitsuru.

In: Tetrahedron, Vol. 58, No. 49, 02.12.2002, p. 9839-9846.

Research output: Contribution to journalArticle

Hayashi, Yujiro ; Yamaguchi, Junichiro ; Shoji, Mitsuru. / The diastereoselective asymmetric total synthesis of NG-391, a neuronal cell-protecting molecule. In: Tetrahedron. 2002 ; Vol. 58, No. 49. pp. 9839-9846.
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