Abstract
Efficient enantioselective syntheses of the functionalized phenol and diethynylcyclopentene moiety of the maduropeptin chromophore were achieved. Their CsF-mediated coupling yielded a sterically congested aryl propargyl ether. The subsequent intramolecular Sonogashira coupling reaction between the vinyl iodide and diethynyl groups occurred at the appropriate position to yield a macrolactam, which was accompanied by Pd-mediated enyne-yne benzannulation.
| Original language | English |
|---|---|
| Pages (from-to) | 3161-3172 |
| Number of pages | 12 |
| Journal | Tetrahedron |
| Volume | 60 |
| Issue number | 14 |
| DOIs | |
| Publication status | Published - 2004 Mar 29 |
Keywords
- Aryl ether formation
- Benzannulation
- Enantioselective synthesis
- Macrolactam
- Maduropeptin chromophore
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Kato, N., Shimamura, S., Khan, S., Takeda, F., Kikai, Y., & Hirama, M. (2004). Convergent approach to the maduropeptin chromophore: Aryl ether formation of (R)-3-aryl-3-hydroxypropanamide and cyclization of macrolactam. Tetrahedron, 60(14), 3161-3172. https://doi.org/10.1016/j.tet.2004.02.020