2014 · CHEMISTRY-A EUROPEAN JOURNAL

Strength by Joining Methods: Combining Synthesis with NMR, IR, and Vibrational Circular Dichroism Spectroscopy for the Determination of the Relative Configuration in Hemicalide

De Gussem, Ewoud, Herrebout, Wouter, Specklin, Simon, Meyer, Christophe, Cossy, Janine, Bultinck, Patrick

Journal
CHEMISTRY-A EUROPEAN JOURNAL
Année
2014
Volume
20
Numéro
52
Pages
17385-17394
Mois
DEC 22
DOI
10.1002/chem.201404822

Abstract

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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