Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Circular Dichroism and Conformations of Pterosins, 1-Indanone Derivatives from Bracken
黒柳 正典福岡 正道義平 邦利名取 信策
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キーワード: conformation of 1-indanones
ジャーナル フリー

1979 年 27 巻 3 号 p. 731-741

詳細
抄録
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.
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© The Pharmaceutical Society of Japan
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