Alkaloids: Chemistry and Pharmacology, Volume 12 by R.H.F Manske, H.L. Holmes

By R.H.F Manske, H.L. Holmes

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Permanganate oxidation of pentaacetylaconine (CXXXI), containing an N-ethyl group labeled a t the carbon adjacent to the nitrogen, produced pentaacetyloxonine (CXXXII) with a residual radioactivity of only 6% of that of CXXXI, 1. THE C I S - ALKALOIDS ~ ~ ~ ~ ~ ~43 clearly indicating that the N-formyl group of oxonitine does not arise from the N-ethyl of aconitine. The original degradative work on oxonitine used in the chemical elucidation of the structure of aconitine ( 7 4 )assumed an N-acetyl group instead of an N-formyl group but a later paper (82)has summarized this work and corrected the structures.

As none of the oxidations produced an acid or aldehyde, it was clear that the analogous C- 18 oxygen functional group of the lycoctonine-type skeleton must be a methoxyl. Carbinolamine ether linkages were rapidly formed with a variety of reagents, leading to the assumption (later shown to be erroneous) (55,60)that C-6 was substituted with a hydroxyl. One of the products of alkaline permanganate oxidation was a carbinolamine ether containing a five-membered cyclic ketone, lending support to the positioning of a second secondary hydroxyl a t C-14 where lycoctonine is analogously substituted with a methoxyl.

Occidentale S. Wats (32)and later from D . An alkaloid named eldeline was isolated 20 S. W. PELLETIER AND L. H. KEITH from D . elatum (33),a plant native to the Altai Mountains in the USSR, in 1952. It was then found that delphelatine was identical with eldeline (35),the latter name being retained by the Soviet workers. elatum, retaining the name eldeline. However, since the compound first named deltaline was isolated many years before the same alkaloid called eldeline, it seems proper that the former name be retained and the latter be deleted from the literature.

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