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 | |
| Publication status | Published - 2002 Dec 2 |
| Externally published | Yes |
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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 journal › Article
}
TY - JOUR
T1 - The diastereoselective asymmetric total synthesis of NG-391, a neuronal cell-protecting molecule
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.
KW - IBX oxidation
KW - Knoevenagel reaction
KW - Natural product
KW - NG-391
UR - http://www.scopus.com/inward/record.url?scp=0037010766&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0037010766&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(02)01290-5
DO - 10.1016/S0040-4020(02)01290-5
M3 - Article
AN - SCOPUS:0037010766
VL - 58
SP - 9839
EP - 9846
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 49
ER -