Studies on Digitalis Glycosides. XXV. Preparation of 14β, 15β-Epoxycardenolides from Odoroside H and Digitoxin.
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概要
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Odoroside H (Ia) was converted into 14β, 15β-epoxy-5β-card-20(22)-enolide-3β-ol-β-D-monodigitaloside (IIIa) in the following reaction sequence : Dehydration of odoroside H diacetate (Ib) with thionyl chloride in pyridine to give 14-anhydrodigitoxigenin-monodigitaloside diacetate (IIc). Mild hydrolysis of IIc with acid afforded the corresponding acetyl-free glycoside (IIa) together with monoacetate (IIb). These 14-anhydro compounds (IIa, IIb and IIc) were treated with N-bromoacetamide followed by alumina chromatography to yield 14β, 15β-epoxy-5β-card-20(22)-enolide-3β-ol-β-D-monodigitaloside (IIIa), and its mono- and diacetate (IIIb and IIIc) respectively. Microbiological deacetylation of IIIc furnished IIIa. In the same manner, digitoxin tetraacetate (VI) was changed into 14β, 15β-epoxy-5β-card-20(22)-enolide-3β-ol-β-D-tridigitoxoside (VIIIa).
- 社団法人日本薬学会の論文
- 1966-10-25
著者
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佐藤 大助
Shionogi Research Laboratory, Shionogi & Co., Ltd.
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堀江 美恵子
Shionogi Research Laboratory, Shionogi & Co., Ltd.
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佐藤 大助
Shionogi Research Laboratory Shionogi & Co. Ltd.
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堀江 美恵子
Shionogi Research Laboratory Shionogi & Co. Ltd.
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