Circular Dichroism and Conformations of Pterosins, 1-Indanone Derivatives from Bracken

概要

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Pterosins and pterosides, 1-indanone derivatives isolated from bracken (Pteridium aquilinum var. latiusculum), and the derivatives exhibit CD Cotton effects associated with n→π^* transition of conjugated ketones in the range of 310-370 nm. Snatzke's rule was applied to the compounds and the conformations of the indanones were discussed from the observations by the CD. The conformation of pterosin A type compounds having a hydroxymethyl group at the 2-position is affected by the intramolecular hydrogen bonding. In pterosin C and L type compounds bearing a hydroxyl group at the 3-position, the hydroxyl group exists in pseudoaxial conformation irrespective of the configuration at the 2-position. The results obtained by the compounds of the established stereochemistry by chemical methods were applied for the determination of the absolute configurations of pterosin D type compounds.
公益社団法人日本薬学会の論文
1979-03-25