THE PAPILIONACEOUS ALKALOIDS: XIX. THE STRUCTURE OF LUPANOLINE

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Abstract
Lupanoline which contains both a carbonyl and a hydroxyl group was reduced by lithium aluminum hydride to β-isosparteine. The identity of β-isosparteine was established by its conversion into sparteine by dehydrogenation and subsequent rehydrogenation. Attempts to acylate lupanoline resulted in the formation of anhydrolupanoline which was hydrogenated to dihydroanhydrolupanoline, a compound also obtained by the direct oxidation of β-isosparteine.It is concluded that lupanoline is 2-hydroxy-17-oxo-β-isosparteine.

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