1964 年 84 巻 11 号 p. 1067-1071
Besides acetic acid and cinnamic acid, anhydrotaxininol was obtained previously by the hydrolysis of taxinine, desdimethylamino derivative of taxine, an alkaloid contained in Taxes baccata L. and two kinds of substances, alkylanthracene and β-acylalkylnaphthalene, produced with the selenium dehydration reaction from anhydrotaxininol, were obtained, but their structures had not been determined, because of a very minute amount. In order to increase a yield of dehydration product, selenium dehydration reaction was carried out with anhydrotaxininol by the LiAlH4 reduction and alkylanthracene was mainly obtained, without β-acylalkylnaphthalene production. The determination of alkylanthracene structure was attempted synthetically analyzing their ultraviolet and infrared spectra, and, among the alkylanthracene derivatives synthesized, 1, 2, 3, 8-tetramethylanthracene was found to be identical with the dehydration product by melting point depression and infrared spectra. This fact quite agree with the estimated chemical structure of anhydrotaxininol proposed by Uyeo, et al.