Abstract
The diastereoselective aldol-type reaction of a γ-pyrone via a sodium anion has been developed. This reaction is useful for synthesizing γ-pyrone-containing natural products. Also, we applied the Mukaiyama aldol-type reaction of silyl enol ether of γ-pyrone by using TiCl 4. This Mukaiyama aldol-type reaction of γ-pyrone indicated higher anti-aldol selectivity than the aldol-type reaction of a γ-pyrone with NaHMDS.
| Original language | English |
|---|---|
| Pages (from-to) | 6477-6484 |
| Number of pages | 8 |
| Journal | Tetrahedron |
| Volume | 68 |
| Issue number | 32 |
| DOIs | |
| Publication status | Published - Aug 12 2012 |
| Externally published | Yes |
Keywords
- Diastereoselective aldol-type reaction of a γ-pyrone
- Mukaiyama aldol-type reaction of a γ-pyrone
- anti-Aldol selectivity
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Cite this
Takemura, T., Hayakawa, I., Fukasawa, E., Sengoku, T., & Kigoshi, H. (2012). Toward the synthesis of γ-pyrone-containing natural products: Diastereoselective aldol-type reaction of a γ-pyrone. Tetrahedron, 68(32), 6477-6484. https://doi.org/10.1016/j.tet.2012.05.111