A synthesis of (±)-Δ2-α-Lycoren-7-one,the key intermediate for the total synthesis of (±)-lycorine |
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| Authors: | Bunsuke Umezawa Osamu Hoshino Shohei Sawaki Haruki Sashida Kazuhiko Mori Yoshinori Hamada Katsumi Kotera Yoichi Iitaka |
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| Institution: | Faculty of Pharmaceutical Sciences, Science University of Tokyo, Shinjuku-ku, Tokyo 162, Japan;Shionogi Research Laboratory, Shionogi & Co. Ltd., Fukushima-ku, Osaka 553, Japan;Faculty of Pharmaceutical Sciences, University of Tokyo, Bunkyo-ku, Tokyo 113, Japan |
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| Abstract: | (±)-α-Lycoran-3,5-dione (14a) was prepared from octahydrophenanthridin-3-one (8b) obtained by two methods starting from 5-aryl-4-nitrocyclohexene (2) and 1-hydroxyl-2-aryl-5-oxo-cyclohexanecarboxylic acid (10), both of which were prepared by the Diels-Alder reaction of 3,4-methylenedioxy - ω - nitrostyrene with butadiene and the Robinson annelation of 3,4-methyl- enedioxy - phenylpyruvic acid (9) with methyl vinyl ketone, respectively, 14a was converted into (±)Δ2-α-lycoren-7-one (22b), which has been transformed into (±)-lycorine (1) by Torssell |
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