37 独活(ウド)の成分研究 : ジテルペンアルデヒドの自動酸化について

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  • 37 STUDIES ON THE CONSTITUENTS OF ARALIA SPP. : AUTOXIDATION OF THE ALDEHYDES OF SOME DITERPENES

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Isolation and structural determination of the diterpenes (I, II, IV, V, VI, VII, VIII and IX) of Aralia cordata and A. racemosa have been reported. During the course of the study, we have encountered that some of the axial aldehyde at C-4(IX, XIII and XVI) were quite unstable especially in solution and were rapidly autoxidized on standing at room temperature by neither irradiation nor addition of radical initiators. The structure of the degradation products(IX→I and X; XIII→II, XIV and XV; XVI→XVII, XVIII, XIX, XX and XXI) and the reaction sequence in each case were elucidated. The structural dependence and the mechanism of this reaction were discussed. (c.f. Chart 1) The present finding would be significant in relation to the studies on biosynthesis and chemical synthesis of the 4-hydroxy-18(or 19)-norditerpenes such as XXXVIII, XXXIX, XL, XLI, XLII and XLIII which have been recently found in plants.

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