Studies on Digitalis Glycosides. XXV. Preparation of 14β, 15β-Epoxycardenolides from Odoroside H and Digitoxin.
- 1 January 1966
- journal article
- research article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 14 (10) , 1133-1137
- https://doi.org/10.1248/cpb.14.1133
Abstract
Odoroside H (la) was converted into 14,15[beta] -epoxy-5[beta] -card-20(22)-enolide-3[beta] -ol-[beta] -D-monodigitaloside (IIIa) in the following reaction sequence: Dehydration of odoroside H diacetate (Ib) withthionyl 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 14[beta] ,15[beta] -epoxy-5[beta] -card-20(22)-enolide-3[beta] -ol-[beta] -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 14[beta],15[beta] -epoxy-5[beta] -card-20(22)-enolide-3[beta] -ol-[beta] -D-tri-digitoxoside (Villa).This publication has 3 references indexed in Scilit:
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- Steroids and related products. XXIII. Cardiotonic steroids. I. The synthesis of 14β-hydroxy cardenolides. Part ISteroids, 1964
- Die Glykoside von Nerium odorum Sol., 3. Mitteilung. Die Konstitution von Odorosid G. Glykoside und Aglykone, 95. MitteilungHelvetica Chimica Acta, 1952