著者

柳屋 光俊 続木 一夫 渡辺 隆啓 中島 康之 松田 冬彦 長谷川 和夫 松本 毅

出版者

天然有機化合物討論会

雑誌

天然有機化合物討論会講演要旨集

巻号頁・発行日

no.22, pp.635-641, 1979-09-20

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Pederin, a potent insect poison isolated from paedrus fuscipes, exhibits various interesting physiological activities, such as inhibition of mitosis in HeLa cell and blocking of protein synthesis at concentrations of 1-10 ng/me. We describe here the first total synthesis of pederin. Asymmetric Synthesis of Pedaldehyde Derivatives. Asymmetric reduction of ketone 14 was examined under various conditions. The desired alcohol 13R was obtained by reduction with LiAlH_4 in ether-toluene (54: 46) at -123°in 74% e.e. The alcohol 13R was converted stereoselectively to pedamide 28 (Fig. 4,5). Synthesis of N-acyl aminoacetals. A new general method for the synthesis of N-acyl aminoacetals was developed and the method was applied to the synthesis of pederin, starting from (+)-pederic acid and (+)-pedamide.