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- W2024333063 startingPage "157" @default.
- W2024333063 abstract "The alkaloid delsoline (C25H41O7N) was oxidized by acid permanganate mostly to dehydrooxodelsoline, and by neutral permanganate to anhydrohydroxydelsoline. Oxidation of the alkaloid with mercuric acetate produced anhydrohydroxy-N-de-ethyldelsoline which could be re-ethylated with ethyl iodide, thus showing the presence of an N-ethyl group in delsoline. Anhydrohydroxydelsoline was also obtained from O-acetyldelsoline perchlorate by oxidation to an anhydronium salt followed by hydrolysis with sodium hydroxide, and this method of preparation provides evidence of its carbinolamine structure. O-Acetyloxodelsoline, obtained from acetyldelsoline, is cleaved by lead tetra-acetate to a secodiketone that loses the elements of methanol on recrystallization. Hence the base contains two vicinal tertiary hydroxyls, one of which is β to a methoxyl group. Dehydrooxodelsoline is also cleaved by lead tetra-acetate and the product undergoes an internal aldol rearrangement. These results are interpreted in the light of a structure that is tentatively suggested for delsoline." @default.
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- W2024333063 date "1958-01-01" @default.
- W2024333063 modified "2023-10-05" @default.
- W2024333063 title "A suggested structure for delsoline" @default.
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- W2024333063 doi "https://doi.org/10.1016/0040-4020(58)88014-x" @default.
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