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Updated: Mar 1, 2026

Atomic Scale Structural Studies of Macromolecular Assemblies by Solid-state Nuclear Magnetic Resonance Spectroscopy
Published on: September 17, 2017
Stereochemical assignment of fusiccocadiene from NMR shielding constants and vibrational circular dichroism
Christian Merten1, Michael Dirkmann2, Frank Schulz2
1Organic Chemistry 2, Physical Organic Chemistry, Ruhr-University Bochum, Bochum, Germany.
Abstract:
The absolute configuration (AC) of the common precursor of the fusicoccane family of terpenoids, fusicocca-2,10(14)-diene (FCdiene), had only been deduced by a lengthy total synthesis, or indirectly from crystal structures of fusicoccin A. However, in particular the AC determinations based on downstream products of the terpene synthase intrinsically overlook potential epimerization reactions. In this contribution, we confirm the relative stereochemistry of FCdiene by comparison of experimental and predicted 13 C-NMR chemical shifts, and finally determine the absolute configuration from an analysis of its infrared and vibrational circular dichroism spectra.
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