Studies on the Sapogenins of Dioscorea tokoro Mdkino. II The Structure of Tokorogenin
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- Morita Katsura
- Takeda Research Laboratories
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説明
(1) The correlation of tokorogenin (I) with the known steroid, 25D-5β-spirostan (IX), was established: Tokorogenin formed an acetonide (IIa), which could be tosylated and then hydrolyzed to give tokorogenin monotosylate (IVb). On treatment with alkali, IVb was led to anhydrotokorogenin (Va), which on oxidation with Py.—CrO3 and subsequent reduction with CrCl2 gave rise to an α,β-unsaturated ketone (VII). Catalytic hydrogenation of VII followed by the Huang-Minion reaction furnished 25D-5β-spirostan (IX).<BR>(2) In order to determine the configuration of the hydroxyl group at C3, IIa was oxidized with Py.—CrO3 and the product was reduced with LiAlH4 to give a mixture of IIa and XIII. Careful chromatography of the mixture revealed that the substance eluted first was XIII, while the second which eluted from the column was IIa, thus leaving only the structural possibility of 25D-5β-spirostan-1β,2β,3α-triol (I) to tokorogenin.
収録刊行物
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- Bulletin of the Chemical Society of Japan
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Bulletin of the Chemical Society of Japan 32 (8), 791-795, 1959
公益社団法人 日本化学会
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詳細情報 詳細情報について
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- CRID
- 1390282679107505152
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- NII論文ID
- 130001958831
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- ISSN
- 13480634
- 00092673
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- Crossref
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可