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

Yujiro Hayashi; Junichiro Yamaguchi; Mitsuru Shoji

doi:10.1016/S0040-4020(02)01290-5

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

Yujiro Hayashi, Junichiro Yamaguchi, Mitsuru Shoji

Research output: Contribution to journal › Article › peer-review

25 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 language	English
Pages (from-to)	9839-9846
Number of pages	8
Journal	Tetrahedron
Volume	58
Issue number	49
DOIs	https://doi.org/10.1016/S0040-4020(02)01290-5
Publication status	Published - 2002 Dec 2
Externally published	Yes

Keywords

IBX oxidation
Knoevenagel reaction
NG-391
Natural product

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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AU - Hayashi, Yujiro

AU - Yamaguchi, Junichiro

AU - Shoji, Mitsuru

PY - 2002/12/2

Y1 - 2002/12/2

N2 - 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.

AB - 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.

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KW - Knoevenagel reaction

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KW - Natural product

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