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Concise synthesis of stagonolide-F by ring closing metathesis approach and its biological evaluation
- Source :
- Bioorganic Chemistry. 37:46-51
- Publication Year :
- 2009
- Publisher :
- Elsevier BV, 2009.
-
Abstract
- The first total synthesis of 9-membered macrolide, stagonolide-F (3), starting from commercially available 1,5-pentane diol is reported. A combination of Jacobsen's hydrolytic kinetic resolution (HKR) and Sharpless epoxidation is used for the creation of two stereogenic centers, while ring-closing metathesis (RCM) strategy was used for the construction of the lactone ring. The molecule synthesized exhibited potent antifungal, antibacterial and cytotoxic activities against all the tested strains.
- Subjects :
- Sharpless epoxidation
Antifungal Agents
Stereochemistry
Diol
Microbial Sensitivity Tests
Ring (chemistry)
Metathesis
Biochemistry
Stereocenter
Kinetic resolution
Heterocyclic Compounds, 1-Ring
Inhibitory Concentration 50
Lactones
chemistry.chemical_compound
Ring-closing metathesis
Cell Line, Tumor
Drug Discovery
Humans
Molecular Biology
Chemistry
Organic Chemistry
Total synthesis
Stereoisomerism
Anti-Bacterial Agents
Cyclization
Macrolides
Subjects
Details
- ISSN :
- 00452068
- Volume :
- 37
- Database :
- OpenAIRE
- Journal :
- Bioorganic Chemistry
- Accession number :
- edsair.doi.dedup.....48bf3a37e4bb540be16a7c34e5bb4179