Totalsynthetische Untersuchungen an Steroiden. VI. Einfuhrung der C-Substituenten in die angulare Stellung der kondensierten Ringsysteme. (1). Einwirkung von Kaliumcyanid auf rac-D-Homo-18-nor-androstan-derivaten.
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概要
- 論文の詳細を見る
Durch Einwirkung von Kaliumcyanid und anschlieβende Acetylierung lieβ sich rac-3β-Hydroxy-D-homo-18-nor-5α-androst-13 (17a)-en-17-on (I) unter der 1,4-Additionsreaktion des Cyanidions und nachfolgender Verseifung glatt in die epimere Brucken-Verbindung, namlich (13〜17) β-sowie (13〜17) α-Laktamol (IV), (V) und deren Acetate (VI) und (VII) verwandeln. Ferner wurden durch Abanderung der nachtraglichen Reaktionsfolgen, z. B. Alkylierung und Acetylierung oder Oxydierung, eine Reihe von beim C_<13> epimeren C_<17>-Alkoxylaktamolen, z. B. (VIII), (IX), (X), (XI), (XX) und (XXI), synthetisiert. Die 13-Cyanverbindungen, wie (XV), (XVI) und (XVII), konnten erst durch kurze Einwirkung von Kaliumcyanid auf (III) oder durch Verwendung einer begrenzten Menge von Kaliumcyanid an (I)-Acetat (II) hergestellt werden. Die raumlichen Strukturen aller hierbei erhaltenen Verbindungen wurden ermittelt. Die hier eingefuhrten Reaktionsfolgen stellen eine neue Method fur die Einfuhrung der angularen C-Substituente dar und lieferten einen Anhaltspunkt zur Totalsynthese der normalen sowie 18-funktionierten Steroide.
- 社団法人日本薬学会の論文
- 1961-10-25
著者
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永田 亘
Forschungslaboratorium, Shionogi & Co., AG.
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青木 務
Forschungslaboratorium, Shionogi & Co., AG.
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武田 健一
Forschungslaboratorium, Shionogi & Co., AG.
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寺沢 唯夫
Forschungslaboratorium, Shionogi & Co., AG.
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青木 務
塩野義研
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武田 健一
Research Laboratory Shionogi & Co. Ltd.
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寺沢 唯夫
Shionogi Research Laboratories Shionogi & Co. Ltd.
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Takeda Ken'ichi
Shionogi Research Laboratory Shionogi & Co. Ltd.
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