The enzyme inhibitor RK-682 (5R)-(+)-1 was prepared in solution and on a solid support from (2R)-glycerates in five steps and ca. 40% overall yield. Key steps were a ring-closing tandem addition-Wittig alkenation reaction of the respective protected or immobilized glycerates with the ylide Ph(3)PCCO and the 3-acylation of the tetronic acids thus obtained with palmitic acid. A similar route extended by a mesylation-elimination sequence led to antibiotic agglomerins A-C 2 featuring 3-acyl-5-methylidenetetronic acid structures.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jo050797i | DOI Listing |
Publication Analysis
Top Keywords
enzyme inhibitor
8
inhibitor rk-682
8
antibiotic agglomerins
8
solution-phase solid-phase
4
solid-phase syntheses
4
syntheses enzyme
4
rk-682 antibiotic
4
agglomerins enzyme
4
rk-682 5r-+-1
4
5r-+-1 prepared
4
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!