AI Article Synopsis
- The retro-Diels-Alder reactions of diketo-1,3-dioxin-2-ones yield alpha,gamma,epsilon-triketo-ketenes, with the reaction temperature significantly lowered by adding a 2-phenyl group.
- These ketenes, produced at 78°C, can be reacted with alcohols to form resorcylate esters, which are further modified through reactions with cesium acetate and trifluoroacetic acid, resulting in aromatization.
- This technique was successfully used in the total synthesis of resorcylate antibiotics W1278A, -B, and -C, where the assembly of monomer units happens during the formation of the aromatic ring.
Article Abstract
The onset temperature of the retro-Diels-Alder reactions of diketo-1,3-dioxin-2-ones to generate alpha,gamma,epsilon-triketo-ketenes was found to be significantly reduced with 2-phenyl substitution. These ketenes, generated at 78 degrees C, were trapped with alcohols to provide resorcylate esters following aromatization by sequential reaction with cesium acetate and trifluoroacetic acid. The methodology was applied iteratively to the total synthesis of the resorcylate antibiotics W1278A, -B, and -C. It is noteworthy that in this process the linking of the monomer units occurs during construction of the aromatic ring.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jo9015858 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!