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Neolignan and lignan glycosides from branch bark of Davidia involucrata
1Department of Bio-engineering & Technology, Huaqiao University, Quanzhou, Fujian, PR China. maouyang@hqu.edu.cn
Journal of Asian Natural Products Research
|September 22, 2007
Abstract:
Two new neolignan glycosides, davidioside A (1) and davidioside B (2), have been isolated along with six known compounds from the branch bark of Davidia involucrata. Identification of their structures was achieved by 1D and 2D NMR experiments, including (1)H-(1)H COSY, NOESY, HMQC, and HMBC methods as well as FAB mass spectral data.
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Preparation of Diols and Pinacol Rearrangement
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.

