Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 52, Pages 17385-17394Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201404822
Keywords
circular dichroism; configuration determination; natural products; NMR spectroscopy; structure elucidation
Categories
Funding
- Pierre Fabre Laboratories
- CNRS
- Ghent University
- CalcUA core facility
- Hercules Foundation
- Flemish Government department EW
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The relative configuration of a key subunit of hemicalide, a recently isolated, highly bioactive marine natural product having potent antiproliferative activity against a panel of human cancer cell lines, was assigned by combining stereocontrolled synthesis of model substrates with NMR, IR, and vibrational circular dichroism (VCD) spectroscopy. The assignment of the absolute configuration of asymmetric carbon center C42 in two structurally complex epimeric substructures containing six stereocenters by VCD analysis illustrates the power and reliability of combining methods.
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