Control of asymmetric biaryl conformations with terpenol moieties: Syntheses, structures and energetics of new enantiopure C2-symmetric diols
2008
New Enantiopure Diols from Terpenes
publication
Evidence: high
Author Information
Author(s): Y. Alpagut, B. Goldfuss, J.-M. Neudörfl
Primary Institution: Institut für Organische Chemie, Universität zu Köln
Hypothesis
The study investigates the synthesis and properties of new enantiopure C2-symmetric diols derived from terpenes.
Conclusion
The new enantiopure chelating diols are efficiently synthesized and exhibit flexible biaryl axes that are conformationally restricted.
Supporting Evidence
- The new diols are based on (−)-menthone, (−)-verbenone, and (−)-carvone.
- X-ray analyses confirmed the preferred biphenyl conformations of the synthesized diols.
- Computational evaluations supported the stability of the observed conformations.
Takeaway
Scientists made new types of molecules from natural substances that can help in making better medicines. These molecules can twist in special ways that are important for their use.
Methodology
The diols were synthesized through the addition of 2,2'-dilithiobiphenyl to various terpenes followed by hydrolysis.
Digital Object Identifier (DOI)
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