15 Rhoeadine及びAlpinigenineの全合成
書誌事項
- タイトル別名
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- 15 The Synthesis of Rhoeadine and Alpinigenine
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Rhoeadine (I), which occurs in a variety of plants of the genus Papaver of the Papaveraceae, is an alkaloid of the group characterized by its 3-benzazepine structure. In connection with our synthtic studies of ochotensine and related alkaloids, we have worked out a route to rhoeadine starting from the intermediate (VII) for the synthesis of ochotensine and applying a Wagner-Meerwein rearrangement which resulted in enlargement of the isiquinoline ring. The spiro-isoquinoline (VII) was treated with ethyl chloroformate and triethylamine to give the urethane (XX). This was methylenated with methylene iodide and potassium carbonate in dimethyl sulphoxide to furnish the dimethylene-dioxy-spiro-isoquinoline (XXI). Treatment of this with lithium aluminium hydride gave the N-methylamino-alcohol (XXII). The alcohol (XXII) was treated with methane sulphonyl chloride and triethylamine in dry tetrahydrofuran to give a mixture of unsaturated amines (XXII) and (XXIV). Oxidation of the allylamine (XXIII) with osmium tetroxide gave the diol (XXV). Treatment of (XXV) with sodium metaperiodate followed by sodium borohydride, gave (±)-rhoeagenine diol (V), m.p. 142-143°whose i.r. (CHCl_3), Mass and n.m.r. spectra were superimposable upon those of rhoeagenine diol from natural sources. The same sequence of reactions starting from dimethoxy-spiro-isoquinoline (XXIX) gave the α-glycol (XXXIII) which was subjected to oxidation with periodate followed by reduction with lithium perhydro-9b-boraphenalylhydride to yield alpinigenine diol (XXXV). The diol (XXXV) was converted to alpinigenine (III) by oxidatione with manganese dioxide.
収録刊行物
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- 天然有機化合物討論会講演要旨集
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天然有機化合物討論会講演要旨集 15 (0), 107-114, 1971
天然有機化合物討論会実行委員会
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詳細情報 詳細情報について
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- CRID
- 1390282681050496768
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- NII論文ID
- 110006677646
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- ISSN
- 24331856
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- CiNii Articles
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- 使用不可