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

33 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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10.1016/S0040-4020(02)01290-5

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

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.",

keywords = "IBX oxidation, Knoevenagel reaction, NG-391, Natural product",

author = "Yujiro Hayashi and Junichiro Yamaguchi and Mitsuru Shoji",

note = "Funding Information: This work was supported by the Sumitomo Foundation and Grants-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan. The authors thank Drs H. Osada and H. Kakeya, of RIKEN, for sending us NMR data for NG-391 and for helpful discussion throughout the course of this research. The authors are grateful to Shinetsu-Kagaku Corporation for the gift of TBSCl.",

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doi = "10.1016/S0040-4020(02)01290-5",

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T1 - The diastereoselective asymmetric total synthesis of NG-391, a neuronal cell-protecting molecule

AU - Hayashi, Yujiro

AU - Yamaguchi, Junichiro

AU - Shoji, Mitsuru

N1 - Funding Information: This work was supported by the Sumitomo Foundation and Grants-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan. The authors thank Drs H. Osada and H. Kakeya, of RIKEN, for sending us NMR data for NG-391 and for helpful discussion throughout the course of this research. The authors are grateful to Shinetsu-Kagaku Corporation for the gift of TBSCl.

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.

KW - IBX oxidation

KW - Knoevenagel reaction

KW - NG-391

KW - Natural product

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DO - 10.1016/S0040-4020(02)01290-5

M3 - Article

AN - SCOPUS:0037010766

SN - 0040-4020

VL - 58

SP - 9839

EP - 9846

JO - Tetrahedron

JF - Tetrahedron

IS - 49

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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