25 シキミの有毒成分,Anisatin,Neoanisatinの構造

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Two toxic compounds, anisatin (I) and neoanisatin (II) were isolated from the seeds of Japanese star anise, Illicium Anisatum L. The structure of anisatin was already determined as (I). The properties of two toxic compounds are similar, except that the 1,2-glycol is present in anisatin whereas not in neoanisatin. Correlation of two toxic compounds was investigated: two-step oxidation of neoanisatin (II) gave a ketoacid which is identical with the acid (VII) (its structure and stereochemistry are known) derived from anisatin. Norneoanisatin (VIII), on oxidation with chromic acid in sulfuric acid afforded a lactone-dicarboxylic acid (IX), the formation of which indicates the trans-fusion of two carbocyclic rings. The structure of neoanisatin was deduced as (II) on the basis of the oxidation products mentioned above and the spectral data. Anisatin (I) was isomerized to a lactone-carboxylic acid, anisatinic acid (XI) under basic conditions. The infrared and NMR spectral data show that the carbon atoms marked with asterisks in (I) are involved in the isomerization. The structure (XI) is presented for anisatinic acid. The structure (XII) was assigned to the acetylated product of anisatinic acid. The corresponding isomerization of neoanisatin (II) was also observed. The intramolecular displacement of the β-lactone moiety by the carbanion is the isomerization, leading to formation of a new carbon-carbon bond. The steric compression of the molecule is responsible fbr this unusual transformation.
天然有機化合物討論会の論文
1966-09-15

25 シキミの有毒成分,Anisatin,Neoanisatinの構造

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