6533b830fe1ef96bd12978a4
RESEARCH PRODUCT
Total Synthesis of (±)-Oxalicumone C and Chiral Resolution and Elucidation of Its Absolute Configuration
Lars AndernachSiegfried R. WaldvogelChristoph WinkTill Opatzsubject
Chiral column chromatographyCircular dichroismChemistryStereochemistryOrganic ChemistryVibrational circular dichroismAbsolute configurationTotal synthesisPhysical and Theoretical ChemistryEnantiomerChiral derivatizing agentChiral resolutiondescription
The racemic total synthesis, the chiral resolution, and the elucidation of the absolute configuration of the natural product oxalicumone C were investigated. The goal was achieved by a synthetic strategy beginning with the synthesis of a 5-hydroxy-7-methylchromone precursor. Further modification possibilities were achieved by introduction of a vinyl moiety into the chromone, which was based on a selective iodination step in the 3-position. Further transformations furnished the racemic natural product. To determinate the absolute configuration of naturally occurring oxalicumone C, both enantiomers were separated by chiral HPLC. Comparison of the calculated and experimental vibrational circular dichroism spectra unequivocally indicated that (S)-oxalicumone C is the naturally occurring enantiomer.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-11-06 | European Journal of Organic Chemistry |