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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Solid state structure and absolute configuration of filifolinol acetate
Marcelo A Muñoz1, Alejandro Urzúa, Javier Echeverría
1Instituto de Ciencias Químicas, Universidad Austral de Chile, Casilla 567, Valdivia, Chile.
Natural Product Communications
|August 6, 2011
Summary
Structural elucidation of filifolinol acetate was refined using NMR spectroscopy and X-ray crystallography. This study confirms the molecule
Area of Science:
- Organic Chemistry
- Spectroscopy
- Crystallography
Background:
- Filifolinol acetate (4) is a natural product requiring precise structural determination.
- Nuclear Magnetic Resonance (NMR) spectroscopy is crucial for characterizing organic molecules.
Purpose of the Study:
- To reassign NMR spectroscopic signals for filifolinol acetate (4).
- To independently confirm the structure of filifolinol acetate (4).
- To determine the absolute configuration of filifolinol acetate (4).
Main Methods:
- Reevaluation of 1H and 13C NMR data.
- Single crystal X-ray diffraction analysis.
- Vibrational Circular Dichroism (VCD) spectroscopy combined with Density Functional Theory (DFT) calculations.
Main Results:
- Reassignment of C-10, C-11, and gem-dimethyl signals in the NMR spectra.
- Independent structural confirmation of filifolinol acetate (4) via X-ray analysis.
- Determination of the absolute configuration using VCD and DFT.
Conclusions:
- The study successfully reassigned NMR signals and confirmed the structure of filifolinol acetate (4).
- The absolute configuration was definitively established through advanced spectroscopic and computational methods.
- This work provides a benchmark for the structural analysis of related spirocyclic compounds.
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