47 光学活性を有する新フェニルプロパノイド類の構造ならびに絶対配置

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We have isolated three optically active phenyl propanoids [wutaiensol (2), wutaiensal (3), and methyl demethoxywutaiensate (5)], and a related compound [wutaialdehyde (4)] from Xanthoxylum wutaiense Chen (Rutaceae), which was used as a piscicidal plant in some district of Formosa. Their structures involving absolute configurations were established. Three compounds (2, 3, and 4) were intercorrelated by the facts that 2 was converted into 3 by oxidation with MnO_2 and transformed into 4 by oxidation with OsO_4-NaIO_4. Diagnostic inspection of the PMR spectrum of the dimethoxy derivative (13) which was derived by Baeyer-Villiger oxidation of 4 followed by methylation and that of wutaialdehyde (4) itself gave a clue on the structural establishment by synthesis. 4 was prepared from 19 according to the synthetic sequence shown in Chart 2. These evidences allowed us to depict their plain structures as formula 2, 3, and 4, respectively. The absolute configuration of 2 was established by correlation with S-rutaretin methyl ether (23). Treatment of the S-hexahydrorutaretin methyl ether (24) by partial acetylation followed by phosphorylation and then Birch reduction gave the alcohol (26) which was obtained by catalytic hydrogenation of 2. Both derivatives are unequivocally identical involving the signs of their CD curves. Separately, the phenolic group in S-hexahydromarmesin (27) was removed by the same reaction sequence to give the alcohol (29). Identity of this material (29) with a sample of the alcohol which was prepared by catalytic hydrogenation of 5 followed by reduction with NaAlH_2(OCH_2CH_2OMe)_2. This evidence established the structure of 5 involving its absolute configruation. In a preliminary examination on biological activity, weak but distinct piscicidal activity of 3 and 5 has been shown.
天然有機化合物討論会の論文
1982-09-10

47 光学活性を有する新フェニルプロパノイド類の構造ならびに絶対配置

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