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 |
Keywords
- IBX oxidation
- Knoevenagel reaction
- NG-391
- Natural product
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Cite this
Hayashi, Y., Yamaguchi, J., & Shoji, M. (2002). The diastereoselective asymmetric total synthesis of NG-391, a neuronal cell-protecting molecule. Tetrahedron, 58(49), 9839-9846. https://doi.org/10.1016/S0040-4020(02)01290-5